I'm not purporting to speak for the entire east coast nor the entire west coast, but from my personal experience having lived 4 years in Daytona Beach and 7 years in St. Pete, I would have to say that the West coast blows away the east coast - generally speaking of course. There are hot spots like Jacksonville, Ft. Lauderdale and Miami which are friendly to boating, but mile-for-mile of coastline, I'd take the west coast any day. From Clearwater to St. Pete to Tampa to Sarasota to Ft Myers to Marco Island to the Keys, it's beautiful, and the boating amenities are plentiful. Generally speaking again, the Gulf is typically calmer, clearer, warmer and more boater friendly - simply because of it's size and depth.
Speaking of flights, Airtran flies from Tampa or Sarasota to St. Lois Direct, for typically 150 bucks round trip.
Classes?: Ya, there are a ton. Local West Marines hold classes and St. Pete has a huge Coast guard base with many USCG power squadron instructional classes and groups - of course, wherever you end up, I'm sure there are dozens of OSO members who would be more than happy to show you guys the "ropes," myself included.