DO NOT go to Pine Hills!!!! EVER!!!!!
Noted. Avoid Pine Hills.
I suggest you rent first then you are free to look around.
That was part of our original plan. I was going to teach for 4 more years and my wife for 3. During that last year, we were going to rent in the area and she was going to scout housing while I finished up teaching and packed up our house. With the changes likely to be coming down in the next year with our new school board, we may both be done at the end of next year (so, in 1.75 years) and figuring out some plans...
Orlando is a hot market, right now. There's a lot of building going on. If you want to live close to WDW, I would recommend either Windermere, Hamlin Grove or Winter Garden in the Horizons West region. All are a 10-15 minute drive from WDW. I'd recommend making a trip just to look around in those areas. My realtor was fantastic and I'd be happy to recommend her.
Just know that you'll see wide swings in the monthly HOA dues. If you want a 2 bedroom, Celebration has 2 bedroom condos. It's expensive, though.
I bought a 3 bedroom townhouse in Waterleigh. The final phase is under construction, so there are models to tour. I have just under 1600 square feet, open floor plan downstairs, all bedrooms upstairs and a half bath downstairs. One car garage.
I understand your concerns after the election. Funny you mention Scotland. I've been thinking of Wales, but keeping my house in Winter Garden.
I think the recommendation to rent for a year is a good idea. That way you can take your time and get to know the area before buying.
Most likely looking for a fully detached single family home. Most condos and townhouses will not allow me to exist in them - piano, bass guitar and low brass instruments do not play well in any kind of shared wall situation.
I lived in Scotland in the early 1980s and we went back and visited a few years ago with our daughter - if the weather was better, northeast Scotland would be our plan.
If your local agent represents one of the major carriers, that shouldn't be a problem with changing coverage to a new home. As you're looking in the Central Florida, not coastal area, I don't think you'll find too much difference in insurance rates.
Do you pay state income tax in Maryland? Because we don't in Florida. Property taxes may be lower, also, we have a $50K homestead exemption in the state.
Most new construction, at least in my neighborhood, is concrete block with stucco. It would take a bomb to cause major damage to my house. I'm pretty sure as long as my roof was okay, I'd have very little structural damage with a Cat 3 hurricane. The big issue would be flooding, so check to see if the area you are looking in is in a flood zone. You'll need federal flood insurance or you won't get a mortgage. And many have solar panels on their roofs.
My agent does major carriers, but not one that is in Florida - but he has connections and has treated us very well over the years.
Yes, we have income tax and a 'healthy' property tax. I figured on flood insurance being a decent expense just about anywhere in Florida. Also, expect HOA to be an expense as well. Not looking forward to the HOA thing - I've been lucky enough in the four houses I've lived in to never have to deal with one.
Thanks for all the insight and the neighborhood suggestions!