David,
Here are a few brief answers to your questions. As you peruse through TOTV you'll see these and a number of other topics on living in TV covered.
Historic side.... all single family dwellings, from very small single wides to very spacious modular homes and some stick built homes. Nothing really "side by side"...you might have seen pictures of courtyard villa sections where houses are separated by a wall or fence.
Minimum age...this is a 55+ community but by law up to 20% of the homes can be sold to those under 55; so, age is not an issue. There are a number of under 55 residents.
Shopping abounds in the near vicinity...either by golf cart or by car. Everything is within a few miles. From the historic side, you have to cross 441 via a bridge to get to most shopping by golf cart. Banner mercantile sells a detailed map. Someone else on here can give you better guidance on ordering one over the phone.
Grandchildren are welcome and can use most of the amenities...bocce, shuffleboard, family pools, etc (Golf over the age of 10 paying a guest fee). Some pools are designated adults only (must be over 30) but there are a number of all-age family pools for residents and guests.
Golf...the executive courses are 'free' as part of your amenity fee (if you walk); if you ride, there is a $3.50/person trail fee; Or, you can buy an annual trail fee for your household residents for about $142. Exec courses are primarily par 3's with one or two par 4's thrown in. Check out the golfing the villages website for lots more details. Championship courses charge green fees.... as little as about a $1 a hole in the summertime up to $54 a round, for residents, in the winter.
Buy now, rent it out options.... on the historic side, you're probably only going to rent for 3-4 months a year (Jan-Mar or Apr), so, factor that in.
Golf/Heat... depends on how you tolerate heat; in the golf cart is easier than walking this time of year. I play at all hours of the day but I tolerate heat pretty well. Usually some cloud cover and a breeze at the peak heat of the day and the humidity starts to go down after noon.
OK, that'll get you started. Best suggestion is to thoroughly read through TOTV and come see for yourself.
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Maryland (DC Suburbs) - first 51 years 
The Villages - next 51 years
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