We purchased a condo in Kissimmee (5 miles west of Animal Kingdom) 6 years back. Resort Management was later taken over by Wyndham Vacation Rentals, however we've never had our unit in the rental program anyhow. It's primarily used by our family for a few weeks a year, with the occasional rental to acquaintances. Depending on where and what you purchase, monthly HOA alone, can be very high. Between HOA, Management fees, insurance, electricity and Property Taxes, you can easily be paying over $10,000 USD annually in certain areas/Resorts. Also, because we do rent occasionally, we're required to have a business license (renewed annually), have to pay State, Municipal and Tourist Tax, and we have to file US income tax each year (times two, as my wife and I are co-owners).
We purchased at a time the CND dollar was at par with US, and housing prices were still ridiculously low, so despite the declining CND dollar over the years, and the increase in HOA and other expences, we're still managing okay. We always have the option of putting our unit in the program, should the dollar plummet further. Occupancy rate is about 74% for our resort, which is good, however I've spoken with other owners who advise that both the wear and tear on their units, and limited return on investment at times (many Resorts will drop prices as low as $70 per night, even if the going rate is $175, just to fill the place), can be frustrating. There's also consideration of Capital Gain tax if and when you sell. Paying Capital Gains in the US, generally means you don't pay twice (in Canada), however if like us, you purchased when the CND dollar was worth more than USD, then sell when it sits at 73 cents, the Canadian tax grab will want their share of the difference. Just a few things to think about. I now have an accountant in Canada and Florida, something I didn't really consider before the purchase. This would have been necessary anyhow, as when you eventually do sell, you have to submit a US tax return for each year you owned the property.
I will say that the purchase was easy however, less complicated than buying in Canada. No lawyer involved, my real estate contact (also my property manager), walked me through it. Other than a 3-day trip to look over some Resorts, everything was done by email/fax (offers, counter-offers, purchase). I just retired in November so I have more freedom to come and go, however with my wife still working and a kid in high school, I still won't be spending months at a time at Disney. But it's been a great ride so far. And we've been Annual Pass holders for a few years now. One of the perks. Cheers!