I’ve got a segment like that locally too, short, steep, and super punchy. My first time up it I was on a bike with 50/34 and an 11-32, had to walk twice because it was so bad, finished in 4:00+. Next year I had a new bike with a 50/34 11-28 and some more fitness and did a 2:57. Following year (last year) I was on a 52/36 11-28 with even more fitness, did a 2:37.
This year on same gearing with some TR under my belt, I did a 2:19 averaging over 500w, set my 1 min power PR at 656w. Was at 190bpm+ for about 2 minutes and ended up placing 8th out of over 1000 people. The 2:02 KOM is set by a rider whos 50lbs lighter than me, so unlikely to ever snag it, but all I wanted was to be in that top 10 with some local legends. If I can shave another 4 seconds however, I’ll be in the top 5, but I really don’t even want to think about attacking that hill again this year.