Hi Cardiologist from a native Toledoan.
I've been lurking here on your thread a while. I think you are accustomed to assimilating large amounts of data and facts and creating a coherent whole from them. I'm not sure that is the best way to approach this tractor idea.
Given your career and related activities, kids to raise, and family to think about, I think a tractor would most likely fall into the hobby category for you. I would choose one or two things you would like to do well, and focus on what is needed to do that. Taken too far, you are only making more busy work for yourself, perhaps.
Take the PTO generator for example. It will be useless to your family if you are not there to hook it up and connect it to your power. If you happen to be low on diesel fuel, that's another chore. If some other implement is mounted on the 3-pt hitch, that has to come off first of all. If the generator has migrated to back in some corner, that's more work to get it out. If you get it going, leave for work and the utility power returns, your wife isn't likely to know, or want to know if she is anything like my wife

, how to switch back over. There are much better residential generator solutions that are hands-off, automatic operations.
You could rent a small tractor-loader-backhoe (TLB) like a Deere 110 to dig stumps. You would have the satisfaction of having done it yourself without sizing your tractor to backhoe requirements, or storing the backhoe attachment 99% of the time while it is idle. If you don't have an equipment shed, the weather and exposure will kill it eventually while it sits in any case.
I guess a tractor and some outdoor activity would be therapeutic after repeatedly telling over-weight middle aged guys to get some exercise and stop smoking. :laughing: But, I would try to focus on maximizing your enjoyment, and minimizing your hassles.
BTW, you have to rank among the world's worst gardeners :laughing: if you cannot grow tomatoes and peppers in Toledo, or you just cannot commit the time needed to tend them to maturity. That could be a clue, but only you know.
Sorry for butting in, but it is germane to your original question. Good luck and have fun.