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Dick -
There have been a whole raft of boats on this forum that started in way, way worse shape than the boat you're looking at. The questions you're asking are the questions you'd ask if you were comparing it to a like-new boat. The questions I'd ask are a. how much money will it take to get it into sailable shape, and b. how much time (my own work) do I want to put into it to get it into sailable shape. Of course, if you are a perfectionist or are into restoration work, that is a whole other ballpark. There are folks on the forum who've truly restored their boats to like-new condition, but most of us settle for something well less than that just to get out on the water. These boats are over 30 years old, after all.
Dividing your questions into money and time: standing rigging is not expensive, running rigging is cheap, hardware is fairly expensive but you probably don't have to replace it all and can hunt for sales; sails are expensive new - main $700-$900, jib $400-$500 - but again you might not need to buy both at the same time and both Shurr and North have sales in the wintertime; bailers and bailer work are labor-intensive but not terribly expensive, $125 per bailer plus epoxy and your time; hull repairs as with the transom are time-intensive but not hugely expensive (see attached Whaler hull repair link for a repair on an area worse than yours); the brightwork on this boat looks positively glorious in comparison with where some have started - it is hard to tell from the picture, but it looks as though the horizontal wood just needs refinishing, the vertical wood (which is plywood and tends to rot and delaminate) may need replacing. Again you're talking about $120 in wood and your time.
So the question centers around how much of this you want to take on. You may find a fully-restored 5.2 somewhere, but it is likely to fetch $4,000+ and you'll have to wait forever until one pops up. In the meantime, if you can get this one for something less than $1,500 or so including a trailer (can't see if it is on one), you will likely be sailing this summer and will have no lack of wintertime projects to keep you busy. (Trailer - inspect it as well. If exposed to salt water it may need a new axle and wheels - $180 and a weekend - or a new one for as much as $600-$700)
Just my perspective, but I'm a "turn the rough side down" kind of guy.
Bob V
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