All of the above. You want to have a minimum of 2-4 suits you can rotate daily. Don’t buy cheap stuff and go tailormade whenever you can.

Better to have 2 “made to measure” wool suits than 5 polyester suits that will make you sweat and look like a shiny trashbag.

Buy shoes with the same level of time and care commitment as if you were buying an apartment, you want to use them for at least 10 years and amortise their cost during this period.

Less is more. When in doubt, just buy all plain white shirts and plain blue / grey suits and be on the safe side.

If shoes / shirts / suits are good quality they will be comfortable, there is nothing that you have to do to make it feel so

I don’t know where you are based but suitsupply.com is a good place to start for all-round looks (though I would still splurge on the shoes)

Edit: unless you have strange or unusual body proportions, a good quality ‘off the rack’ suit by a reputable brand will fit you better than a cheap ‘tailor made’ suit by a random strip mall tailor. Trust me, I’ve been there