I'm one of those people that are terrible about under or over torquing things, and therefore relate to using a torque wrench on everything.
The filter and drain plug however is probably one of the few exceptions I've not bothered with.
The "trick" that I use with the drain bolt, is to push it tight, and not pull it. This is just using the short handle of a standard 3/8" ratchet.
The filter, I just follow the instructions of turning 1 or 1.5 revolutions, after the filter's lubricated gasket makes initial contact with the block. Then I'll turn it back slightly, to make it easier to twist back off by hand, some 3-6k down the road.
I was also pretty bad about cross-threading things. The trick to avoiding this is to turn counter-clockwise until you feel a light drop or bump, then immediately start to turn clockwise.