I have a 23' Class C that has been fabulous for getting around and staying at regattas. However, I'm beginning to question the advantage of 7mpg to the keys vs. staying in hotel (break even is about 4 nights). For weekend regattas a couple of hours away it's spectacular! All the gear stays in the RV and the beer is cold when you get there.
If I were to start over again, I would do like you and look for a Class A in the 26 to 30' range. I initially bought the 23' thinking that it would be convenient to go to the store if we needed to and that the fuel mileage might be better...turns out it really doesn't matter if it's 23 or 30 feet long, the fuel mileage is pretty much the same. It is nice when we need to make a trip to the store but it's still a pain and we do most of our shopping before the weekend. I wouldn't rule out a class C because the cab-over sleeping area is nice when you have guests and you can get more value in them usually. Although my cab-over has an entertainment center with 19" TV, I do sometimes wish I had a bed available up there.
If looking at Class Cs (or all of them for that matter), take a good look at the wheel bases. Rear wheels that are farther back are a good thing when it comes to handling. Adjustable air bags on the rear end are nice to tailor your ride to the road - especially if their adjustable on the fly from the dash.
I highly recommend finding an RV with leveling jacks - they're prohibitively expensive to add later and not really worth it after the RV purchase although you WILL bitch and moan about having the manual jacks constantly.

Generators are the first items to be neglected on a used unit. They really need to be started and run with load for an hour at least once a month or the carburator suffers. A carb rebuild on a typical Onan will run about $350 to $400 - do it yourself for about $80. You can almost plan for that.
Upgrades that I have made:
-- no trailer hitch existed, had to weld one in place because of rear frame construction
-- CB Radio (vital for monitoring traffic on long trips and finding work arounds)
-- Satellite radio (sirius)
-- Upgraded stereo
-- trailer light isolator so they have their own circuit (I had a trailer light short take out my anti-lock brake module, my engine CPU, and all the running lights at 11pm somewhere in florida).
-- RV Bilstein shocks
-- Airbag suspension under rear end for more suspension travel
-- modified AC sine wave inverter for entertainment center so we can watch TV / movies from house battery without generator (also powers new rope lights for proper 'mood' lighting)
-- mast mount on roof was mounted until I could extend trailer tounge