I wouldn’t, if I were you — from what I understand (and in my experience), a better way to avoid soreness is to work the same muscles three days in a row. Unless you have an actual injury to heal up, waiting until the soreness goes away just means you spend more time being sore (which, in addition to being no fun, is not good for motivation.)

Twenty pounds isn’t a horrible starting point for upper body, depending on the exercise in question, and a lot of how much weight you should be working up to depends on what your goal is for working out. When I was doing a lot of martial arts and fighting competitively, I would do a lot more lower body weight and do more reps with less weight on the upper body so I stayed toned and lean without building too much extra muscle mass that might push me out of my weight class and make my cardio work harder. I’d only add up to my maximum weight range a couple of days before a fight right before stepping in to spar–it was like swinging a weighted bat before stepping up to the plate, it didn’t make me stronger, but it did make my hands faster.

I’m guessing your overarching goal isn’t beating down another fighter (if it is, two words: wind sprints) but I’m guessing it’s not being a body-builder, either. So chin up! :-)

The eight minute mile is one of my more immediate goals.. starting slow though, as I’m not much of a runner.

Simply reducing the amount of soda I drink has helped incredibly. My wife pretty much does all the cooking, and she’s a health nut, so that doesn’t hurt either.