That's one of my biggest frustrations - I wasted a lot of time on reprompting. I was making myself stick to 100% LLM approach for a while, in order to learn.
I can't say for everyone, but for me it's hit-and-miss: if LLM starts with "Oh, sorry, you're right" that's a STRONG signal I have to take over right now or rethink the approach, or I get into the doom spiral of reprompting and waste half a day on something I could've done myself by that point, with only difference that after half a day with a coding agent I discovered no important domain or technical knowledge.
So, "how much" to me depends so very much on seemingly random factors, including the time of the day when Antropic decides to serve their quantised version instead of a normal one. On non-random too, like how difficult the domain area is, how well you described it in the prompt, and how well you crafted your system queries. And I hate it very much! At this point, I'm trigger-happy to take over the control and write the stuff that LLM can't in the "controlling package" and tell it to use it as an example / safety check.