Yes, as a buyer in the market today, you must have a sense of humor and a high tolerance for frustration.
I have seen quite a few project boats in the 25-30' range that are advertised as sailaway condition for a $5-10K price, but have serious problems such as rotten decks, cockpit soles, or bulkheads, severely corroded keel bolts, interior waterline marks indicating a past sinking, rigging
problems, and/or original 30 - 40 year old sails or engines in need of immediate replacement that make the boat basically worthless. The sellers don't seem to understand the cost of their deferred maintenance or the serious problems with their boats.
I am now wary of the seller who has had the boat for only a year or two, and wants to sell, or someone who is selling for a "friend". I think some are given these boats, or picking them up on eBay or from charitable auctions, with a number of problems, including a blown engine, then fixing only the engine (usually an A4), and trying to sell the boat as if that were the only problem and the boat is now in overall fine condition. I suspect the blown engine was usually not the only problem, but the final straw that caused the previous owner to give up.
There are also some unrealistic sellers who refuse to recognize the economic conditions and the fact that there is an oversupply of boats at reasonable prices. Their price would have been realistic 5years ago, but not now. So, their boats are sitting there unsold for months on end, waiting for the promised economic turnaround, while they pay another years slip fees or the cost of bottom paint