Orlando pro/con questions

[Marty G.]

Hi group, Here's a question I'm posing to the group. Currently looking to relocate to Orlando area. I have a few 3 families that are in my home of CT. Here's the dilemma. Since I don't know the area in Orlando very well, I have a job that allows me to call anywhere home and the Orlando area is a place that I'd like to invest in due to its proximity to parks and a potential job offer for my significant other. What I was wondering is, does it make fiscal sense to perhaps buy a house in a vacation area, use it as my own house? During this time we can decide if we like the area, while searching for other areas (perhaps less touristy) and if so, purchase an additional home in a traditional residential area and use the "vacation" home as a rental? My rationale is that if we don't like the area/job/etc, I still have a vacation rental I can use to generate some income while we decide the next area to claim as the primary residence. I also have the flexibility of purchasing more properties in CT, which I know better, and skipping the vacation market altogether in FL and sticking to just residential non vacation rentals in Orlando. The cons of this are that many residential neighborhoods don't allow for rentals, so if we tried these areas and decided it wasn't for us, we would then sell as a traditional home as opposed to a renting it as long term rental or vacation home. I also realize I could rent for a period of time and evaluate but again, then I'm paying someone else's mortgage that could ultimately working towards my own. Any suggestions? PS - the jobs that my girlfriend would be offered would be at the parks, while I have the flexibility of working from anywhere, which is why I wanted something close to the parks (for her commute). Thanks! Marty