All of the boats you mention can be a lot of fun and can handle lake Michigan. My wife and I owned 3 Catalina's and an Endeavor 42 during our 44 years of sailing.
I used to describe the boats quality with an auto industry analogy. The Catalina's were Chevy's, built well, last a long time and reliable. The Endeavour was a Buick, a Chevy with a little extra polish. If you are cruising, you will be pleased with the extra's you find in the Endeavour. If you plan to drive to the marina over the weekend and go
day sailing, you will like the Catalina, although the 36 is a big
boat for that.
All boats made in the 80's have potential issues, and if the previous owners have not taken action to mitigate the damage or potential damage you may be
buying a problem. Both owner communities are very active on social media, and you will find the owners very helpful in both identifying issues and helping with the
repairs.
Soft decks are more common on the
Great Lakes because
wood rots faster in fresh
water and also you have the freeze thaw cycle. Some of the 80's boats had foamed in Tankage, the Endeavour 42 did, and replacing the
tanks is quite a job, not too expensive if you are a DIY'er with some time, but very expensive if you are paying someone to do it. Soft decks can also be fixed by a good DIY'er.
Regarding the use of a
surveyor, buyer and seller beware, they are not always worth the investment. We recently
sold our Endeavour 42, and the
surveyor who was supposed to be very knowledgeable made some very bad assumptions about things at one point mistakenly condemning a
thru hull because he mistook the white
lithium grease on a rim for Caulking without even bending to feel it and telling the buyer the 35-year-old
diesel needed a complete
rebuild or replacement even though we had an
oil analysis and a
current engine survey by a well-recognized
mechanic.
If you do buy a
used boat from the 80's, plan on getting heated
winter storage, at a place that will allow you to
work on it and use the
winter break in sailing to fix up the boat to your liking so you can spend the summer sailing.
Closing thought, if your
DIY skills are lacking or you simply cannot make the time to
work on the boat, I suggest you spend the extra
money and get a newer, maybe smaller boat.