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Going from “What If?” to “Why Not!”

Every 100 days that tick by we have a small celebration; a special meal, a movie, or we watch our Disney vacation home movies with our favorite desert. So here we are at 799 days. This time we have decided to share a little of our celebration with everyone here. It has been 255 days since we started our countdown on August 13, 2009. That was the day that we decided to stop talking about our dream, and actually start to pursue it. We were at 1054 days at the start, a number that seemed at times gigantic.

We had tossed the idea around like so many others have. “Hey, what if…” Then, on that one August day, we both started to ask ‘Why Not…!’ We decided on July 1, 2012 for a few reasons. Our oldest daughter is in high school, and will graduate that year. My youngest daughter will finish grade school and move on to middle school. It just seemed like a perfect year to answer the perfect question.

We decided to take some time during this post to give you an update on where we are on our relocation efforts and some of the research we have already done.

1.       Employment

This is clearly the most important factor in any decision that is made in just about any aspect of life. How will I earn my income? Right now, Florida has one of the highest unemployment rates in the nation-this is due mostly to the high amount of tourism and construction related jobs that were lost. I work in the Information Technology industry, which has been effected along with everything else in our current economy, just not as hard. Florida, and more specifically, the Orlando area, has a high concentration of technology related jobs, so I have found numerous opportunities even today.  It is our plan for me to really start looking for employment sometime during fall of 2011. If I were to find fulltime employment before July 2012, we have discussed a few options, including me moving early.

2.       Housing

 Where will we live? This is probably going to be just as difficult, if not more, than finding that job. Where you live is so very important-it is where to find your rest and relaxation from the outside world. While I wish we could just live at Caribbean Beach Resort, we will have to settle for something off Disney Property. Since we have always focused on Walt Disney World during our trips to Florida, it has been very interesting researching the area outside the gates. I have found that there is a tremendous amount of very nice apartments that are on just about every corner. We have decided to focus on the Kissimmee and Windermere areas. They both have extremely nice apartments that have 3 bedroom 2 baths, and are not outrageously priced. During our next vacation to Florida in November, I have decided to take a full day and drive around some of the areas that I have researched online. This will give me a great feel for the area that I could never get from a photo. I plan to check out apartments, and the general area around a few of them. How far is it to the closest grocery store? Is it an area that is crowded with tourists? We will try to find that delicate balance of being close to Disney World, but not too close that we are crowded every day. There are apartments that are so close you could throw a stone and hit something on Disney property.  I have also learned in my research that there are a tremendous amount of rental homes in the area. These are wonderful homes in beautiful neighborhoods that are also reasonably priced.  The current economy has also provided a very large amount of low priced homes to purchase. While we are not looking to buy right away when we move, we may look into it more after we have been there for a little while, and are more comfortable with knowing exactly where we want to live.

 3.     Schools

Since we have children that are school age, researching the school system in the Orlando area has also become very important. My oldest daughter will be entering college when we are ready to move, so it will be a little easier for her. Right now she is looking to study Computer Animation. She is currently enrolled in a charter school in our hometown that focuses on art, so she is very committed to her choice. We toured one university in Orlando during our last trip, and on our next one, we plan to visit the college that she would really like to attend – Ringling School of Art and Design in Sarasota. It has been rated many times as the number one college in North America for Computer Animation. While the choice seems set, it is a little more complicated for my younger daughter. She will be entering 7th grade in 2012. I have done a fair amount of research on the school system in the Orlando area and in Florida in general. It seems like there is a high commitment to excellence in education in the state, which is reassuring. The neighborhoods that I have looked at have some very nice, highly rated middle schools. Another option that we are beginning to research is eSchool. eSchool allows the student to take classes from home over the internet. It is a fast growing way to get a very good education. There is still a lot more that we need to look at regarding that, but it is nice to know that there is an option in the event that she struggles with a new school – something that is always at the back of our minds.

4.      Moving

Another big item to consider is how are we physically going to move our family across the country? We have looked at every option from hiring a moving company to come in and pack it all up, to renting a moving van ourselves. We have so far decided to sell a great deal of our stuff, including most of the furniture, and move only those possessions that cannot be replaced; clothes, toys, major electronics and memories. We currently have mostly a jumble of mismatched end tables, night stands, dressers and so on, along with living room furniture that is at the replacement stage, so we will have one gloriously large moving sale, and plan to purchase new items when we arrive at our new place. That is an expense that we will research as well so we can be prepared. The goal is to have everything fit into one of those do-it-yourself moving vans, such as uHaul, and recruit my parents to drive it down for us (something they have already expressed a high interest in. Who wouldn’t look for any excuse to travel to Florida anyway?) We have found the prospect of getting rid of a lot of the things we have accumulated over the years both refreshing and overwhelming. We currently have a full size basement that we make well use of, and have come to realize that those are very rare in Florida. We are already going through just about everything we have to see if it passes that ‘do I need it now’ test.  Something I am sure we will do often over the next year and a half.

 There are also a large number of things that I have researched that do not fit directly in to those categories. I have looked into the DMV, and what we need to do in order to change our license, and get those beautiful Florida license plates for our vehicle. (I think I will cry a little the first time I put that plate on my van!) Hurricanes are something that we really don’t have to worry about too much in Wisconsin. We have spent some time looking at what are some recommended preparedness kits, and what to do in the event that a hurricane approaches the Orlando area. We are blessed to live in a very low crime rate community, and while the Orlando area has a higher crime rate in general, many of the communities that we have researched are very safe areas to raise a family. And, maybe one of the most important items, that Florida Resident WDW Annual Pass. We will most likely have annual passes before we move down, but it is nice to know that Disney recently changed their policy to allow the renewal of Annual Passes for Florida Residents to be paid in monthly installments. That will be helpful to do instead of paying a large amount at one time for 3 or 4 passes.

While there is going to be a lot more research to come, it is my hope that we could give you a glimpse of where we have gone so far. There have been a number of you who have mentioned you would like to make the same move at various times in the future, so I hope we can make that relocation a few steps easier. It is my plan to do this again every 100 days or so.

We also want to take a quick minute here to thank everyone for following us on our journey, and for the tremendous support. The community of Disney fans is like no other, and it is so exciting to be able to talk about this with people who really share the passion that we do.


  1. I’m in IT as well and someday I hope to move my wife and I to Celebration, we both haven’t been to Disney world since 1993, but we are going this Xmas to explore it. We are both madly in love with Disneyland, we got married there last month, and we are even thinking about joining the DVC, but celebrationnhas always been a goal of ours, only time will tell.


  2. As someone who has already gone thru this process, I’ll let you know some stumbles I had on my journey to Fl.
    [1] I wanted to make the move before I retired so that I’d have more chances of making friends here. Unfortunately my impressive (I was told) resume did not help the fact that I didn’t have a local address when I applied for jobs. Employers couldn’t be sure I was serious & not change my mind. I got a job finally & moved but the economy tanked shortly after. 18 yrs with the same company does not prepare you for 3 jobs in 5 yrs! Have a backup plan – I brought my part time job with me & it’s been a constant source of sanity for me 🙂
    [2] My daughter had gone through some changes so she packed up her daughter & they moved with me. We lived in a hotel in the area we were looking at. We didn’t have to worry about breaking a lease as I’ve heard from others, when they found the house they wanted. This was a perfect way to get to know a neighborhood, check out traffic & different ways to get to same spot (traffic jams are common, especially in tourist season).
    [3] Sarasota is lovely (my son-in-law is from there) & your daughter will like the area, I’m sure. And you’ll have a mini vacation spot to go to as it’s only about a 2 hr drive from Kissimmee/Disney.
    Since you are looking at eschool, you might want to also check out home schooling. My older grandaughter exceled in day care, prek & kindergarten. But by the time she entered 1st, her teachers were having trouble keeping her occupied as she whizzed through her assignments. My daughter researched home schooling & started her on an online program & then switched to home school. Lots of resources available. Rory goes on field trips with other home schoolers. Only difference is that she doesn’t sit in a classroom all day & she’s still ahead of the mark for her age.
    Feel free to contact me, if you like, with any questions. Having already gone through all this & hearing from co-workers what they went through, I’m more than happy to help someone avoid some of the pitfalls we encountered.
    Happy planning – hope to see you @ Disney in November. We’ll be there as always 🙂


  3. If you ever think of Sarasota it’s beautiful and only 2 1/2 hrs from Disney. We go up and it’s the stay overnight and take mini vacations throughout the year. The schools in Sarasota are some of the beast in the state. And of copurse then your oldest could goto Ringling which is just the beast!
    Good luck in your journey for relocating to Florida! I know I’ve been here almost my entire life and don’t want to leave!


  4. I like your plan and you seem to have everything covered. My only comment is that being there and going to Disney on a daily, weekly, monthly basis would loose some of the charm in making that special trip and staying on property. I’ve been for just a day trip and I’ve stayed for extended trips on property and in my opinion staying in one of the resorts makes it so much more special!! Part of the magic for me is the planning and anticipation of the trip and then making scrapbooks afterwards filled with all the special memories. I don’t think I’d want to trade that feeling.


    • Hey Susan!

      We have discussed that very topic many many times – would we loose the ‘Feeling’ we get after that long drive from Wisconsin, knowing that we are so far away from the distractions of every day life.

      While we do plan on gonig to WDW just about every day for at least that first month – we have still committed to staying on property at least once a year for an extended vacation. We are actually hoping to buy into DVC after being there for a few years – once things get settled. Doing that will help insure ourselves that we will have a wonderfully long vacation on property at least once a year. Being there will also allow us to explore some of the areas of Disney World that we never seem to have enough time for on our regular vacations.

      We are also very much looking forward to some of the little things that we could not possibly do from here in WI – going to all the incredible special events that are at WDW – whether it is simply a meet of the month from our favorite podcast group, a book signing from a special author or artist, or any of the other numerous day events that are held throughout the year.

      Another benefit that we will certainly enjoy is being ‘able’ to enjoy a vacation every once and a while somewhere outside of Florida. We have always wanted to travel to other parts of the country, and have planned some vacations from time to time, but it always comes back to “If we are gong to spend this kind of money, and time, why aren’t we gonig to Disney World?” – We could never imagine our one vacation for the year, and it not being at Disney.

      Thanks for your comment! Trust me – this is something that we will most likely continue to talk about – makeing sure that ‘feeling’ is not lost. It is my true hope that once we are there, we can write that we still have that same feeling, along with so many new ones that we thought never possible!



      • Thanks for answering my post! I’m sure that if you love Disney so much that you’re willing to move there permanently, you will not loose that feeling! 🙂

        I did like and agree with your point about being able to go over any time to take part in special events. My husband and I are school teachers and can only get down there in the summer time and I have always dreamed of seeing Disney done up for Christmas! I’m currently saving up for a trip in December when we’ll take a few personal days and make a long weekend of it! Can’t wait!! . . . . . I’ve got that feeling . . .


  5. This is all so exciting and I wish you the best of luck with relocating!! Thanks again for including all of us on your journey. It almost feels as if I’m relocating along with you (Don’t I wish!). My husband and I have always talked about retiring to Cape Cod when the time comes, but on our last WDW trip, Florida was starting to look more and more appealing.


  6. Gosh, you just made my day! I now don’t feel so silly about looking at apartments and potential jobs so early – I’m planning on moving a year from now down to the gorgeous Orlando area. I’ll have a College Degree then, and I sincerely look forward to getting started on my life there. I’m headed out on Friday to go down on vacation and also spy out a few apartments (I’ll let you know if I find some good ones!).

    Thanks for this post! It put me at ease…we’ve got a lot to do!


  7. Sounds like you’ve got your plan pretty much mapped out! We’ve lived in Kissimmee FL for a long time, and love the area. Living this close to Disney and the other attractions is a definite plus.

    I wish you and your family the best of luck!


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