Re: Fun vs Rules - When is too much fun a bad thing?
Well, the point of a game is to have fun, so 'too much fun' is never per se a bad thing. The risk, though, is pursuing immediate gratification at the cost of long term payoff; the PCs should sometimes have to work at things.
However, on your question about tracking, groups vary extensively in how much bookkeeping they tolerate or enjoy. "You didn't prepare properly" is a reasonable cause for a setback or failure, but the required amount of prep should be appropriate to the group.
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