Leaving his relaxed, luxurious lifestyle.
He's currently at 40 trips to his golf resorts although he criticized Obama for being the vacationer in chief lol.
Quitting his TV show
I wish he hadn't. Sounds like he does too.
Spending millions on a campaign
Not really. They were loans, which were often paid out to his own companies: exchanging money in his own hands.
Hurting his reputation, brand and businesses
First, no one hurts the Trump brand like Trump himself. He's responsible for that shit. I don't see how you can blame anyone else. Besides, the whole endeavor of campaigning was a brand-building exercise in the first place.
Sacrificing up to 8 years of being in the most stressful job in the world
Everything he's said makes it sound like he didn't really know that. When compared to his previous life, he "thought it would be easier." He thought he'd just come in and tell a bunch of people "you're fired" and America would be great again. Turns out it's just a bit more complicated than that.
To make more money? When he could easily choose any other strategy
Not so sure about that. Nobody would give him loans not too long ago. Deeply troubling Russian interests have poured money into his ventures time and again and saved him (in case you're wondering why the Russia connection keeps coming up even though it's all apparently "fake news").
The only way he actually would come out ahead is if he has a great presidency
I wish he would have a great presidency. Cause unfortunately he's my president too. I haven't wanted every day to be mired in a new embarrassment or a horrifying misstep. Face it, you got conned. The thing about listening to hateful rhetoric and scapegoating is it's very easy for the powerful to point at someone powerless to divert your attention away from the real problems facing people.
I'm sure he thought people would just do everything he said. Even though that's not how government was designed by the founding fathers. Even though he ran 6 businesses into the ground. Even though he doesn't know a thing about most things (he said "who knew healthcare could be so complicated" ffs).
Otherwise his reputation, brand and profits will be hurt. Call me callous but I could give a fuck what happens to his profits. I'm more concerned about the thousands and thousands of people who are going to die and millions who will suffer because of the "healthcare" plan he and his lackeys in congress are pushing.