I’ve never ran into the limits on the $100 plan, and rarely even get close.

I normally have only one session going at once though.

Same here and while I have multiple sessions going from time to time, my day isn't spent primarily developing software directly anymore (due to role, nothing about LLMs).

I only ever hit the $100/mo limits 1-2 times ever and it was always <1hr before reset (once it was <5min, the other was like ~45min).

I'm even considering going back down to $20 and using extra usage for the times I need to "burst".

Yes but Anthropic made a deal with SpaceX and increase usage limits by 50%, so you might not hit your limits.