Russ, I'm with you on playing with other musicians - big fun and very rewarding. And, while humbling, I always find I play both less and better with really good players.
Through our music co-op I also support and play at jams with various level players. While I always try to be supportive and encouraging, privately I am often amazed at the folks who play in public when their time is nonexistent and their singing is, well, questionable. On the plus side, it's great to see people improve as musicians (a worthy goal for all of us, I suspect).
I love the arranger functions for practice and fun, and definitely see some real possibilites for certain types of gigging, though.
I turned down a blues band gig this weekend to go camping with my wife. The gig paid, yup you guessed it, $100.00. We made more than that per person back in the 70's.