Ashland is pricey, but I love living here. It's liberal, has a university, and the Shakespeare Festival.
Yes, there is a pretty solid boating community between Grants Pass, Medford, and Ashland. There is even a local email list serve that is a great way to meet boaters.
Since you used to live here you may remember- there are several runs (Rogue & Klamath Rivers) close enough for after work or others that take a couple hours (Umpqua, Sac, Box Canyon, McCloud, Pit,Feather). I guess it's just a matter of your willingness to get in your kayak. There is play wave or two that come in every summer and others in the fall. Basically, the only way you will miss boating around here is to just not go
Unless it's flooding, good luck with kayaking Ashland Creek in Lithia Park.
Hope that helps.