Here's what I would look for in your situation. You want something that you practice and learn on for a year or two for the minimum investment.
That goal implies that you don't want something that you spend time and
money fixing instead of sailing. So give a very careful look at the things that need to
work to get you on the
water.
1.
Motor. Will it crank when you turn the key, go into
gear and get you away from the
dock? Do whatever it takes to make sure you aren't
buying an
engine repair project. If you aren't qualified then get a buddy who is or pay a
mechanic a few bucks to check it out.
2. Rig. Check the wires, especially the fittings on the end to make sure the
mast will stay attached to the boat. Also very closely inspect the chain plates, the bolts that attach them to the boat and the bulkheads where they are attached. Don't forget the one at the bow where the forestay attaches.
3.
Sails. OK you are going out to win any races but trying to sail with totally blown out
sails is a drag. First just look at them to see if they superficially look old, stained and ragged. Look at the stitches, especially in areas where the sail may chafe, areas of high stress, etc. Hoist the sails and look to see if they have a smooth curve when trimmed and sailing.
4.
Rudder and
steering. Make sure the
rudder and bearings are tight. Not a lot of slack anywhere in the system.
5. Hoses and through hulls. Make sure these are all in good condition and the seacocks open and close. Good boat doesn't do any good if a hose pops and the boat sinks at the
dock.
6. For your plans maybe not as important unless it got really, really bad. Most boats the decks are built in a sandwich with
plywood or balsa between layers of
fiberglass. Works great until you start drilling holes in it to mount winches and tracks and such. Over time water can leak in and
rot the
wood core. If you're keeping the boat this is a problem. If you want it for a year or so if the
core rot isn't too bad and the decks are not delaminating I wouldn't worry about it. But I would point it out to the seller and lower the
price.
For a learner most of the rest is just extras.