Michael

Maybe too wholesome? There seemed to be zero consequences to anything that happened.

Mary seems too inviting to an "obvious stalker". Imagine if a man walked up to you, seems fixated on "wanting to talk about [something you enjoy]", then he states, in your own words, how he feels about that something. You wouldn't be concerned that this seemingly random guy just pulled a full sentence out of your brain, verbatim? You'd think he's a online stalker who's finally approaching you.

He almost goes into Charlette's room, but doesn't. He sprints home and in both times, he is obviously upset by something, that, judging by her expression, Mary is catching. She seems to know that this out of nowhere, and something happened to make him almost force himself to propose, but it's never brought up.

You can go back and change things before the baby, "is out" but nothing else will affect the child? Going back before the baby is conceived and being 5 seconds late to to the bedroom or even to finishing doesn't matter?

"We can't travel to the future." Then how are you traveling back to your new future after changing your past? Shouldn't they now be stuck wherever they travel since they never lived through the future they create with changes?

Dad never told him he could take people along with his travels? Did Dad not know that was possible? How did Tim figure it would work? Did Dad know? Is that what happened to Desmond? Too many ride-alongs, but not "built" for it? May have been interesting if so.

Seems pretty rude that he never told Mary either, especially if bringing her along is easy enough to prove it to her.

Also, a point that I guess doesn't entirely matter: as far as we know, Tim is the last male in his family, all his children are female; the ability is over with him. He absolutely would not mind by the end, but that's not a concern of his, or his father's? Guess not.