I've done both (
DVC owner and had a 3bed home with a pool that I rented out). The difference is, IMHO , your commitment to eventually wanting to live in Florida, or semiretire/snowbird to Fl. If you're not able/looking to spend at least 3 months of the year in Fl, then you're going to be better off financially either renting a home ( you can rent direct from owners from $500 per week) or increasing your timeshare ownership ( either DVC or a cheaper off site option). In my experience management charges are higher than you are expecting and you would need to rent your home out for about 30-34 weeks a year to cover all costs Obviously the number of weeks you need do depend on the cost of the house, but as a general rule of thumb most "vacation villas" are minimum 3 bedrooms, 2 bathrooms with a private pool. You'll be looking at a cost in the region of $120,000 plus $10,000 to furnish it as a minimum. For a good development close to WDW it's $150k+ . Most rental companies will be able to provide you with 20-25 weeks a year rentals, but this is dependant on a strong market, that hasn't been the case for the last couple of years. You will need to get "private rentals yourself to make up the balance and this can be time consuming and frustrating.
Another factor to consider is the housing market, IMHO Fl is cheap and there is potential for a sharp increase in prices BUT there need a few things to fall into ( or in the case of California out of ) place.
1) Low interest rates will continue to make people look at their earnings from shares,bonds and other sources ( this is also true for timeshare) , if those earnings continue to remain low people will look at "alternate" investments like vacation property as a way of offsetting future vaca costs.
2) If Florida's government ever get serious about slowing the rate of development and the damage/demands being made on the ecosystem any restrictions they put in place for land use will drive up the price of available land, in turn pushing the price of new houses, in turn pushing the price of existing homes. The measures they have tried so far ( minimal amounts of taxes on new home sales) have had no effect what so ever on slowing development. There is still a lot of land in Florida, but IMHO if the people of Florida wish to maintain their areas of natural beauty they need to act pretty quick before they are too late. The water demands of the existing population are already causing problems, more people/houses is going to increase those problems dramatically.
3) A major earthquake in California ( see previous California comment) which is LONNNNG overdue is going to make people look at "safer" places to live. While Fl does have it's hurricane problems these are not as potentially serious in the Orlando area as they are on the coast. If there were to be a major rush of people looking to move to Fl due to a disaster in Ca, point 2 would become much more valid and the "double whammy" of a lot more people and restrictions on land use would really send land prices rising.
4) America ( like Europe) has high density of populations in the Northern colder areas, with relatively cheap land in the Southern warmer areas. Mostly that's because the well paid jobs are in the North. In the case of the USA it's NY, Boston, Chicago and many of the Canadian cities, in Europe it's London, Paris, Germany and Scandinavia. As those "babyboomers of the 60s" get closer to retirement age many of them are going to look at their relatively expensive "family homes" in the north and realise that A) they don't need a 4 bedroom high cost home as their own kids have moved out and B) COLD winters as you get old really aren't much fun. IMHO there are going to be A LOT of those babyboomers looking to sell up their big houses in and around the expensive cities up north and either move permananly to areas like Fl, Arizona and in the case of Europe Spain, Portugal and rural Italy or at least to have a smaller home/condo in their "home state/country" for the summer and to winter in the sunny south. I feel certain this North to South migration will occur, it just may take 10 years to build up steam.
IMHO you can make a pretty strong case for buying a home in Fl, but it is unlikely to be a zero cost item in the short term. In my own case I would estimate the cost was somewhere between $3-5,000 a year to run the place, but I did get 6-7 weeks "free use" of the place. As this was usually at "peak times" when the rental company could have got renters in the house if you are able to vacation at less busy times ( ie avoid easter, Xmas, July and august) you could probably cut that running cost to $1,000-2000 a year.
Here's a link to a report in the Orlando Sentinel, concerning population growth you may find interesting
http://www.orlandosentinel.com/news...may22,0,6866466.story?coll=orl-news-headlines
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