Sounds like a good opportunity, Dave...if it's not too hard on the wallet. The owner doesn't seem overly uptight, and willing to let you learn on his boat - which is a good sign that he may be fairly easy/reasonable to deal with. The chance to crew in races, I think would be great experience. That's one thing I never did, and really wish I had when I had a chance. I think it's probably the best way to learn some good sail-handling skills.
You sound like I did about 20 years ago when I took all the ASA classes
at the Boston Harbor Sailing Club! Our first few outings were on a 27' Soling, then we did some spinnaker
training on a J24, then for several years I bought the annual membership
to use the fleet of Pearson
26's. I worked right in the city, and would often walk straight down after work on any given day and head
right out for a few hours - often for overnighters if I didn't have to work the next day. If you were lucky, sometimes you could get one of the Albin 27's (with the inboard diesel). It was so much fun.
I did my Offshore
Passage-making trip on the Club's Cal
39's. They used to keep two of them in the Bahamas
(Marsh Harbor) every winter, and you could sign on to crew on the trip down in the fall, or back up in the spring. I flew down there in the spring of '93 and helped bring it up as far as Annapolis
After I moved here (to Nantucket), we bought a 1978 O'Day 27 for about $6,500, sailed it down from Providence, RI and made many trips from here to Cape Cod
, Martha's Vineyard
, Cuttyhunk etc etc. Then we had to get rid of it when we started planning the house, the family
I have a little Daysailer now just to get out on the water
occasionally, and my kids
are now old enough to want to learn - so we're having fun with that. But I'm now saving for the next boat that can actually take us away from this island once in a while! Can't decide if I want to go relatively low maintainance with something like a newer Catalina
25, or with something that I can really fall in love with like an older Pearson
Vanguard. Decisions, decisions...