we are in a place, economically, not seen before...many boats are for sale because of that. Certainly there are cycles, and there are boats that tend to be an "investment". I would not buy a boat, even at today's prices and expect to make a profit and trade up in the next few years.
As the boats go up for sale, many dealers and mechanics are getting out..there is not enough business to sustain their markups. I am looking for about 50 hours service work, but simply not willing to pay $65-90 and hour for unskilled labor. Unless you plan to do the work on an inexpensive boat, factor that cost in to the repair, as many repairs will be quite labor intensive.
For example, where I am, they want over $200 setup charge - just to climb the mast, to repair an antenna mount, or to "look" at a wind instrument....this with the "expert" on the deck, not in the chair. The hourly rate starts when the labor heads up, and stops when they walk up the dock. Needless to say, I will wait or find better help.
Second job - to install HnT system...$2K for parts, $3K for labor plus another $1K in added labor, and oh by the way the labor may go up once we "see what the job entails". Or I can save $1K by taking the boat to Norfolk, as the factory rep doesn't like to travel, but you will have to pay transient slip charges nearby for a month, while he does the install...
So, IMHO, just because there are tons of boats for sale, doesn't make the purchase a "good" deal or will help you sell later. I honestly believe you will see more and more boats for sale, until owners and brokers get real on the $$$...
Best of luck, and there is a real nice Cabo for sale near us, been on the market for over a year and a half..