Other than your question of When to come, I would advise you to contact The Villages by phone and get the answers directly from them. Unfortunately, on this Forum, you may get a lot of different answers and some of them aren't necessarily correct or currently correct. Now, as far as When to come, I would suggest you come during the season that you think you might come if you find that The Villages is right for you. Based on the fact that you are from Buffalo, I suspect you would like to escape from winter so a winter Lifestyle would be a good opportunity to see what "winter" life is like in The Villages. But since you are a teacher, coming during your summer break is your idea, a "summer" Lifestyle visit would be recommended. Regardless, The Villages is an interesting place to be in any season.
My other recommendations to you, if you do a Lifestyle visit, plan to make sure you see ALL of The Villages, not just the new area where they will provide your place to stay. The Villages is REALLY BIG and the areas are quite different in the landscaping and amount of restaurants/stores. So see it all. Second, before you drink the kool-aid (i.e. fall in love with the place) and want to buy a house on your first visit, I recommend you plan to rent for a month or so. That really gives you an opportunity to determine if The Villages is right for you, and it will give you an opportunity to get to know the benefits and drawbacks to each of the areas (North, Middle, and South). Plus, there is no harm in renting each year without having to buy a house right now.
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