Hey Christian, I'm a couple years into ownership, and Ive been outfitting for live aboard cruising that is starting this fall. I considered similar boats to your list and also never really wanted a center board. I ended up choosing Holiday based on the condition of the boat and not necessarily just because it was a Tartan. I am extremely happy with the choice and Tartan 37s I'm general. The boat sails awesome with the board up, points really well, and has better shoal draft than most. I like the fact that we could put the board down for improved pointing but rarely do (like never). We are just going to be 2, but there is plenty of room for 4 for anything but long cruises. I guess you could find a boat with more room but that would also add more expense and complications most instances.
In terms of expensive things that I've spent money on that you may want to have a surveyor check: The rudder pintle may need replaced if it has never been done. Standing rigging could need replaced (this goes for any older boat) Hose that penant goes through under mast may need replaced (usually requires a crane to lift the mast) Hose attached to stuffing box and where shaft exits hull may need changing. If so, coupler may be rusted to shaft, requiring replacement of all (this goes for any older boat)
Those are a few of the things I've done off the top of my head. If you have a yard do them, each one is a thousand or three. More of a list that applies to any older boat.
I haven't had any problems with my bulk heads, and while I'm changing my chain plates, none were in seriously bad condition when I pulled them.
If you find a Tartan in good condition, buy it. This forum has helped me imeasurably immeasurably as I've worked through the above maintenance. If I think of other things, will post up.
_________________ Zach Duncan SV Holiday Hull# 280
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