Generally, a boat that has been raced extensively, will have more wear and tear, though it may be maintained better. Delamination in the deck is something you should definitely look out for in an older boat, particularly if it has had a lot of stuff added to it.
A tiller has two advantages over a wheel. One it's simple and requires little maintainence. Two, you have a better feel for the boat. I singlehand a tiller boat, and have no real problem with it. I use a tiller-tamer to hold it steady for the few minutes I need to be away from it.