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I was a late adopter of disc brakes. Rim brake bikes through my racing team were easy and extremely low cost for me. For the racing and riding I do in Wisconsin that's totally fine.
What changed it for me was doing Belgian Waffle Ride, LA Canyons, Mt. Lemmon, etc. Discs are a big deal on long sustained descents, whether they be technical or not. I remember descending in LA one day in the rain on my rim brakes and it was stressful. A few friends in LA and the Boulder area had rim brake wheels blow out from overheating.
I finally made the switch and it was totally painless. I like my discs, they're problem free, and they enable me to fly down Decker Canyon in LA without that voice in the back of my mind telling me the rims will overheat.
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