I am detecting some wishful thinking here.
Maybe. He had an overconfident opponent last race who underestimated Marylander tax fatigue. The last time the Dems lost to the GOP in this state, they had a very strong challenger for the next round - good old MoM.
First of all, "the country" voted in plurality for Clinton in terms of popular vote. Trump won the election, no doubt about it, but you're acting like he won a 60-40 landslide in the popular vote. The margin was razor thin. It is very debatable about whether he has all that much political capital to spend, especially with hostility from his own party.
Second, the GOP lost horribly in the state of MD. Those predictions that Szeliga would ride Hogan's coattails to victory were laughable in hindsight; she got curb-stomped by Van Hollen like any rational observer would have predicted.
Trump is deeply unpopular in MD, and there's no reason to think that will change. Hogan will stay as far away as possible from Trump.
Hogan won his first term in office during a Democratic presidency. I don't think the president is such a key decider as you think.
I agree. As far as pronouncements about Hogan;s re-election, I'm going to wait until six months before the elections. My crystal ball is broken and my time machine is down for parts.