Join the AGLCA and attend a rendezvous. You will be able to talk to 50-75 trawler owners currently on the LOOP
If you are seriously thinking of doing the Great Loop, I can't think of any good reason not to join. These people have done the Loop, are currently doing it or are planning on doing it.
Just like this forum, don't use that as your only source of information. You will get good and bad information on any web forum. It's up to you to figure out which is which.
Many folks have done the Great Loop and then written books about their experience. amazon.com will have most of these and they are pretty interesting even if you're not planning on doing the great loop.
As for boat shows, these are another resource. A good way to see the insides of many different boats and different styles of boats. With your budget, you won't be buying any of these boats new, but it's a good chance to figure out what you like or don't like about berths, galleys, saloons, cockpits, etc. You can apply what you learn at boat shows to used boats you might consider.
Personally, I think a flybridge is a great feature for a trip like this because you can really see the sights from a flybridge (in good weather). You cruise a boat around the Great Loop to see the country and with a flybridge, you get to actually see it. A flybridge also gives extra "free" room and makes a boat of a given size seem larger.
As for handling, there are basically three choices: Single engine, single engine with a bow thruster and twin engine. I have a single engine with a bow thruster and that works for me. Whatever boat you get, it will take a while to get used to how it handles but they all work.