When you are gaming there is always rules you have to follow. Some GMs follow to the letter and others do the rule following when it's super important. Here are some guidelines I like to follow, being a sort of a middle of the road sort of person.
1) Combat. This is the most important time, in my way of thinking, to follow the rules. This is the nuts and bolts of the rules and the rules make combat more balanced. I'd follow the rules as closely as possible, but if you can't remember them off the top of your head and looking them up will slow down play, just go with your best guess and move on. Fun is more important the rules lawyering.
2) Skills. This is one you can fudge on. If your player has worked hard at gathering all the stuff for a fantastic magic item and he had to adventure long and hard to get them, fudge their roll if need be. One roll should not ruin the fun.
3) Roleplaying. Let the rules be stretched here, though not so far that the campaign is overwhelmed by super ninjas or anything. A swashbuckler making the catch on a chandelier, even though he would have missed, will liven up the moment.
4) My suggestion for knowing the rules is to brush up on the rules relevant to your game that night. If you know there is going to be a lot of combat, brush up on combat. If there is going to be alot of roleplaying, look at skills.
Happy Gaming!
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