Actually, this has been an interesting thread, because it probably echos the process many, if not most of us, (for whom money is an object), when we set out on this particular exercise...ie, finding the best boat we can afford, and which will do what we want to do.
I had a particular style in mind - trawler (Clipper) style coastal cruiser, 34-36' with aft cabin, and I did not want to borrow to finance it, so I had a price ceiling as well. The wife said no, she wanted sedan style with aft cockpit, rather than aft cabin, and you know - she was right. As it turns out the number of times we take friends away over-nighting is way less than I thought (hoped..?), and the fact that virtually all new boats of this design now, (yes - still being produced new - Clipper 34 now renamed 36, but essentially the same), are all Europa style, as these are now called, suggests the 2iC knew something...
Anyway, it caused a longer search, because the sedan/Europa style was much less commonly made in the era I could afford, (ie NOT NEW), but eventually one popped up. But of course, being 1975 vintage, there were issues. It was a bit tired, needed quite a bit of cosmetic stuff doing, but I could see that was well withing my capability, and the chief thing was a survey confirmed my impression that nothing really expensive, or needing expert manpower (read expensive) would be needed to get her 'good to go' as it were. The motor was sound. Huge point..!
The mild steel tanks had rusted on the tops by the usual leaking old teak decks, which the PO had also had stripped and replaced with reinforced non-skid fibreglass decks, and he had also had the stainless steel water tanks converted for fuel. 800 litres has proven more capacity than we ever need, and as I said, the engine was sound - all points proven by still all working fine, ie decks, tanks and engine, now 12 yrs later. I had new food grade plastic tanks for house water made, (they were making do with a bladder type water tank in the lazaret), which I installed myself, and 600 litres water has again proven to be all we ever need.
I have since replaced the hot water tank, engine room floors, totally relined the forward cabin with new teak and much of the water-stained teak under the saloon windows, having sealed relevant leaks, painted the entire topsides with Toplac, and had the hull professionally resprayed. I also installed GPS, new sonars up and down, VHF and CD/radio, myself.
We replaced a rag of canvas over part of the cockpit, with full-framed length/width canvas, extended along the side decks as well, rather like the new models have in hard top.
According to a couple of brokers, I have effectively doubled her value, because she does everything a new boat would do, yet I got her cheap, simply because she was tired and showed it.
So, to the original poster, cseitz91, I say by all means beware, and look at as many similar vessels as you can. But a lot of what you described is cosmetic, do-able by yourself, and the engines effectively needing replacement (possibly the fuel tanks also), gives you a huge bargaining chip. Forget what he says he wants, you work out what new American Diesel (Ford Lehman) replacement engines would cost, plus anything else of significance, and make an offer if the hull and other stuff is as cosmetic as it sounds.
In the end, running might still be the best option, but as psneeld and some others beside myself have pointed out, it ain't necessarily so...but only if the owner is prepared to be really realistic in terms of price.
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