You ask some tough questions! We here in the "Redneck Riviera" are not as sophisticated as ya'll northeners... but we do know a bit about hospitality...
Email me and let me know when you're flying in and I'm sure we can hook you up with someone to get you back and forth!
Hotels are pretty good deals - if you choose to spend a c-note a night you can get some pretty deluxe accommodations. There are also some hotels pretty close to the dojo where Winterfest is being held - but not really walking distance... again - I'm sure it won't be too much of a problem to set you up with a ride back and forth. Public transportation in Orlando is possible - but a touch short of a nightmare to figure out. Taxi's are easiest - calling for one to pick you up is pretty reliable. There are some great rental car deals available too for weekend rates - depending on your budget - and what airline you are flying in on.
I've seen airfares for under $100 between New England and Orlando -even direct flights.
Car rentals can go as low as $35/day in some places. The highways in Orlando are pretty straightforward - not as insane as LA from what I understand! You only have to watch out for the crazy tourists...

But it's pretty easy to navigate - had to be built that way because of the international tourism being the biggest industry.
Check out the hotels that David Berndt recommends on the Winterfest page - and perhaps this forum could be a good place for people to post where they are staying to facilitate some car-pooling...
And again - email me and I'll be happy to help you out!