Yeah, no. That TCJA (aka Trump's tax cut), moved me from solidly in deductions to just under standard deductions. I guess financially it's slightly better, but it doesn't simplify my taxes. Because now I'm just on the limit, so I have to do the itemization work anyway. I do use TT, and did all my itemizing (an evening of work), just for it to say "you get the standard deduction now!"
So I do agree, TT could be much better by explaining the deductions (standard vs itemized) up front and asking if you think you want to answer all the detailed questions.
Mortgage interest was always the big one, so all new homeowners would have to itemize. But mortgage interest goes down over time, so you have to keep doing it every year just to see when it's not enough to qualify.
You can also deduct your home office, as a percentage of the surface of your home and share of the utilities. That's one that might apply to a lot of tech people.
Another big one is charitable donations. Some people give up to $1000 (and more), which could put you over the standard limit.
I think the deductions are really what make US tax complicated for the regular person (businesses are another can of worms). It's like saying: you could pay less tax if you can find of all the ways that the tax code has said you can deduct from your income.