Join Date: Jun 2007
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Hi Al, and welcome to Sailnet.
Probably the sub-forum you want to keep an eye on is "Buying a Boat," right now. That, followed by "General Discussion" and "Gear & Maintenance," would probably contain the info most germane to your current questions.
You are right to consider refit, maintenance and slip/mooring costs.
As to the first: A "good bargain," whether cheap or free, may turn out not to be such a good bargain once you find out what's needed to get the boat in order. This topic, alone, could occupy, and has occupied, pages-upon-pages of discussion. You might start by searching "Buying a Boat" with the keywords "survey" or "surveyor." Posts and threads containing that word should have a high likelihood of containing the kind of information you seek.
A boat that floats is not necessarily a boat that should be floated. A sailboat has lots of stresses going on, especially when the wind kicks up suddenly, maybe you're short-handed, etc. The last thing you need at that point is a rig or other catastophic failure.
Maintenance is variable. Some say budget 10% of the cost of the boat, or it's value, annually. Others use other numbers. It's going to depend on a variety of factors, incl. size of the boat (thus, usually, its complexity), its age, quality-of-manufacture, the condition it's in, and just plain old luck: Good or bad. One thing you can almost be guaranteed: It'll probably be more than you expected or desired.
Slip and mooring fees: Well, those are going to be local. Can't help you with this one at all.
As for getting some experience under your belt: You could try checking local sailing clubs for "crew wanted," but your post kinda tells me you might not be up to the strains of racing right now, so maybe not. You could also join a local sail club and find yourself invited for the more laid-back "around the cans" club races, day sailing, etc. (For example: Our club holds a race each week during the season where starts are based on PHRF ratings, so they're less tense; there's no committee boat, so the start/finish line is only roughly defined; everything is pretty much on the honour system, and nobody really "wins" or "loses." Very laid-back.)