I'm an 8 handicap, and for me Tierra Del Sol is the most "challenging" course here in The Villages. The combination of tree lined fairways, fast greens, good undulations, and trouble spots when you hit long or miss a shot to the side make this course great. It punishes you if you make a bad shot.
Glenview is my 2nd favorite for a challenge... although there is less trouble there, so I can typically recover from a bad shot fairly easily. The other champion courses are wide open for the most part - it takes the combination of a bad shot and bad luck to give you a lie you can't recover from.
If you're looking for real challenge for him, try Otter Creek at The Plantation in Leesburg - now that is a tight course! Haven't played there in about 6 months, so no idea as to what shape it is in.
My son played college golf, and was on the mini tours for several years... his favorite course in the area is The Country Club of Ocala. It's a legit challenge, and is gorgeous as well. They have a member for a day program where you can get a tee time and play. This course is amazing - when my son visits, we always try to get a round in there.
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