I would take a cup of coffee and stroll the dock on Saturday morning and just talk to people. You'll learn a lot about the "local politics" that way. You'll also learn a lot about the personality of the dock (mellow, hard party or somewhere in between).
I would do it a couple of times before buying. Another option is a lease-purchase agreement if the seller is open to the idea. It gives you a chance to try before you buy.
I did both and am glad I did. Another thing is winter storage. Is there a yard nearby where you can haul out for the winter?
95 Catalina 30 Island Time
“Only two sailors, in my experience, never ran aground. One never left port and the other was an atrocious liar" - Don Bamford