Hi pmichetti and welcome to the forum. I've had a Classic for 5 years now and love it. It's relatively light weight (compared with the Adventure and tandoms), easy to paddle, very manuverable and pretty quick. Disadvantages: it's not well set up for fishing (I'm not a fisherman though), it doesn't track exceptionally well and there is no provision for a sail.
Those that have Outbacks really like them also, especially for fishing. They have a reputation for being not too great for paddling and pretty poor at tracking.
I also have a new Adventure; it's great for paddling; tracks well, is the fastest (and therefore has the longest range). The fishermen like it, it has some sailing options that none of the others have, and is definitely the most versatile! It boasts all the latest technology that Hobie offers. It is also the longest and heaviest single in the Hobie fleet if that's an issue for you.
If you just want to paddle, the Quest (which has no pedal capability) has been getting rave reviews -- excellent speed and tracking. But still not as good as the Adventure from what I hear. No sailing capability either in case you were to develop a budding interest later.
Depending on what you're your possible uses are, they each have their advantages. If youy can, try out a couple and see what feels right!
