High maintenance I'll give you (and expensive), but I non of the jeans I own are as comfortable as a nice pair of suit pants and despite the fact that no one would care if I wore a hoodie to work I still wear a dress shirt basically every day because it's just so much nicer.

TBH I don't find jeans terribly comfortable and don't wear them very much. In my opinion--and maybe it's just because I'm used to it--the traditional Friday casual Khaki/Button-down shirt hits a sweet spot for office wear.

If you had your suit tailored and it's uncomfortable then it's defective - take it back to the tailor and explain where it's not comfortable and they'll adjust it for you.

The most comfortable suit is still more uncomfortable than a t-shirt and shorts.

I would agree that a well-made dress shirt that fits well is super comfortable. They are just very hard to come by.

I doubt they're very hard to come by but they'll be expensive. I've had shirts tailored in Asia but I admittedly don't bother with tailored clothing on a day to day basis.

I don't know what to tell you, you're doing something horribly wrong then.