I would rent just outside of The Villages. You can find something for 2 or 3 months in the prime season at around $1700/month in Spruce Creek, for example, and probably cheaper in November/December. That will give you time to properly assess which neighborhood you'd like to live in, whether you want new or pre-owned, what model you'd like. There are other factors to consider as well - how the house sits in relation to the other homes, for example might affect your privacy. If you have a dog you might want a courtyard villa. If you want a central location you might want to consider Mallory Square, or Duval. Or if you want to be close to a particular town square, you'd pick a certain village. Many people do buy on the spur of the moment and come out okay, but there are no guarantees. Let's face it, the prices on homes aren't going to be going up for awhile, you certainly have the luxury of taking your time. Yes you'd be paying rent, but you'd be saving on amenity fees, cable tv, utilties, etc., so you wouldn't be paying that much more. And actually, you can usually find rentals in The Villages proper, cheaper in November and December. If you put your stuff in storage and stayed in a patio villa, there are bargains out there. Good luck, and pm me if you have any questions.