I really liked all of the above!!! It's nice to see the old hands give their opinion on various outboards...need more of that here! That guy who is always on a Minnesota lake with someone named pepper (on Utube) always tries out old small outboards, but never gives an opinion on any of them.
Yes, for me (the OP) this has been a very nice welcome to the community, and thank you all for the constructive and really helpful views (on some forums new dumb questions get flamed!!).
I will see both boats this weekend in person, and do my best to make the right call. Neither package is perfect, it will be difficult to weigh the boats or take the time to get the boats checked before I commit, unfortunately. I think the older 35hp one I will be able to take a test drive on, and a personal relationship with the person who is passionate about whalers and trustworthy may give the nod to that boat (so I feel pretty good the boat is as advertised)-- although he has very little information about the engine history (he bought it from a marina, it had a single female owner who didn't use it much and docked it at the marina) . The other (25hp) is on a trailer and doesn't seem like he can easily put in the water (understandable given our locations etc) so while he can start it I can't get a test run easily, even though that engine is newer and a better fit for me.
Overall, these are package deals-- boat, motor, trailer for 3.5k or so, and these boat/ trailer is around 2.5k+ without engines, so my downside risk on motor is not a huge one, but I prefer not to buy something that is an immediate problem. I had originally thought of buying the boat without motor and buying a new one so that I had a really low breakdown risk, but I need a light motor and the newer ones are heavier, plus these two come as packages and are the boats I want.
I think I go with what #flyingscott says then, which is that there "is no less than ideal motor and buy the best package". I think seeing them in person and test driving one of them may easily make the decision for me.
Hope you all are finally getting some warm weather!