Well, it's going to be a flyer for your first one regardless. Bone up on your twisted wools.
I can only offer one more opinion. Fuck the 'level' thing. Buy a suit that makes you feel like James Bond, even if you're a mail clerk. Cost isn't the sole determinant of that.
If you aren't far off from an average build, you might find a Canali, an Armani or a Zegna fit fantastic near out of the box. Those three are very well built and Rosen back the things they sell very well.
All that said, custom shirts are worth it.
Good reminder - "the rat race" is relatively new to me, after all, in my small town nobody gave two shits about clothing.
Out of the box, Samuelsohn fits the best - Armani pinches too much at my upper back in their cuts, and the sleeves require extensive tailoring anyway. Right now I've got Samuelsohn, CK, Arnold Brandt, and Coppley 1883 in the closet. I haven't tried anything by Canali, I definitely will!