agent teams can help with that, the main agent acts as an orchestrator and spawns sub agents to do the actual tasks it generally keeps the main context from overflowing.
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".
Still, the context window is sometimes too small for my usage.