So for me, I have way more money than time, and if I were to do major mods, I would pay the dealer. But I’m not planning any.

For me also, I would feel that while I am totally capable of doing major engine work, I would feel (right or wrong) that having the work done at an authorized dealer would come with some sort of warrantee period. They screw it up, they pay to fix it. I make a mistake I pay to fix it.

There is an active thread right now where the oil line blew off on a guys bike after having dealer work done. Dealer is fixing the engine.

Same as with cars, I used to do a lot more before everything became so computer dependant. Points, carbs, jetting and such, now are all electronic, and I actually like it. Going over the Rockies, don't have to rejet or readjust stuff.
Now, basically all I do is fluid change.
i do still have a 1953 ****** pickup, and 1960 IH Travelall I can work on, or mor correctly, HAVE to work on, to keep running properly

Not sure being a “man” ever had anything to do with it. Anyone who wanted a harley and could afford it has bought and owned one, man or woman, today or in 1930, and in between. I will agree that with the trend of trade jobs declining over the last 40 years it has lead to a decline in the average person’s mechanical ability. Couple that with your second statement that technology has taken over basic mechanical operation (less user friendly), it was bound to get us to where we are today.

I do know that most everyone that I ride with has mechanical ability and we all work on our own stuff. A few just don’t have the time or the patience to do everything, some just don’t want to. I don’t think that makes any of them less of a man.