Scott, Going along to observing sessions is always a good idea. But I don't think there are all that many choices in scopes in the price range we are talking about here. There are the Dobs and small aperture achromats on flimsy EQ or somewhat more usable AZ3 mount. The Dobs are just so far ahead of the achros in performance that they are the clear winner, unless one has some very good special reason to go with an achro instead. (See
http://www.aoe.com.au/refractors.html for achromats.)
Besides the GSOs, there are also SkyWatcher Dobs worth considering, e.g., at MyAstroshop:
http://www.myastroshop.com/products/reflectors.asp. These have a bit better ergonomics and finish than the GSOs (from Bintel or Andrews). The 8" GSO with 4 eyepieces is a more complete package.
But besides telescopes, you might also consider binoculars. A good 7-10x50 is an essential accessory even if you have a scope.