JD I'm 22 and putting the finishing touches on my boat right now (well, as the weather allows, we're averaging about 30 degree days but Thursday will hit 58 so I'm planning to get working early).
I found a 1975 ODay 27 at a good rate and in good shape. Many are in the $5-$8k range. There is about 6' head room (but I'm 6' 3" but I can stand upright under the companionway hatch to stretch a bit at least).
I'll only be spending summer on it as I live in the north east and not yet equipped for winter living. Slip fees in my area are $110-$140/ft in the summer so I'm certainly envious of your slip rates.
I'm a newbie sailor (I've spent only a few dozen hours in a rhodes 19 and a couple ASA courses in a 34') and imagine I'll catch on to the operation of the boat quite quickly (or at least have a lot of opportunity to practice) once I'm on the water. I'm sure it won't be hard to find someone to teach you a few things about your boat in exchange for them getting to play on it too.
In the meantime I've bought several good books and am going through every square inch of the boat to become not only familiar with this particular boat, but sailboats in general. I'm learning a lot as I read through and follow guides (like those by MaineSail) for buffing topsides, new bottom paint, refitting deck hardware, new gas tank, etc. etc. Also try to find a mentor. I often to speak to a guy (I'd name him but I don't want to share him!
) that often shares his experiences if I find conflicting opinions on forums.
The costs have been higher than expected (and I didn't even have optimistic projections) and there doesn't seem to be an end in sight, but I'm loving it, and I'm going to love the adventures even more once she's in the water.
No matter what, I know I would regret not trying it more than I will ever regret trying it.
Just go for it, read all you can while keeping an eye out for good deals. Don't marry a particular model boat but instead try to see as many as you can so when a good deal pops up you are ready to pounce!