Justin, on a 27' boat if you make a mistake you can still usually fight back and overcome the boat. Something gets stuck you can unstuck it. On a 44' boat...things go the other way around. The boat will win every time there is an argument, unless you know how to outsmart it.
And while a 44' boat will comfortably ride out weather that has a 27 bucking around, again the 44 is going to need a lot more forethought to make it do what you want once it gets another idea in it's head. Little things like reefing the sail will be much harder if you get a late start.
So if you had outstanding weather to the Azores...a 44 won't be too big as long as the weather gods treat you just as kindly.
I'd be more afraid of the possible financial hole. When a boat falls off the stands, the impact travels around in all sorts of ways. Sometimes bulkheads shift and have to be retabbed. On some boats (like Sabre) you may literally have to unbuild the beautiful built-in cabinetry in order to access the hull and the bulkhead tabbing. Surprise! Sometimes tankage shifts or hoses pop. The propshaft, supports, rudder tube, could all have damage that is not obvious to the casual glance. If the insurer offered $200k for the boat--they probably thought it was a total write-off, and depending on their policies (percent of book value) it may need more than a mast and a patch on the hull.
IF you can find a replacement mast, and IF you don't mind having a patch on the hull, as opposed to having at least one entire side of it painted...You might have a bargain. Used masts are hard to find, and once they go longer than 48? 54? feet they become oversize freight and quite expensive to have shipped. Masts are often cut and sleeved (spliced) professionally in order to get them into conventional shipping. Of course, that usually means having the new mast installed at a yard, where they know how to do this. If the new mast isn't identical, many things can still work but that may mean more new hardware, more figuring, more rigging. And if the rigging is 20 years old, ALL the standing rigging and fittings are due for replacement, even without the shock of a fall.
I think you'd want to go over the boat very carefully with your friend, make up a detailed list of whatever the two of you see, and price it out in detail. Also figure in the cost of keeping it in his yard or elsewhere for a long time while you work on it. If the project seems attractive to you, either get the insurance survey that was done. or bring in a surveyor, to see what else you might have missed. If there are no surprises and the price is right, it could be a bargain.
I'd also think a fast thirty grand is not out of line, and that it could easily go into the 40's. If you've never done an engine installation and have the new one installed by a yard? Between that and the mast/rigging, you could probably consume the thirty grand right up front.
If the boat is worth, let's say $100k market value, your friend already got (200-15) 185k for it, so arguably he did all right. You might work up something along the lines of "I'll pay you $$ less the cost of the repairs I have to put in" with a list of what you expect, and an agreement that surprises will come out of the purchase price as well. That kinda protects everybody. Still, that's going to be a big job.