I'm not saying this is the right approach, but in the past I've generally just bought the cheapest Cane Creek/Ritchey/name brand loose-ball headset I could find. Sometimes they are ugly and not the smoothest but functionally they've all been fine.

I've shyed away from cartridge bearings due to fear of the hassle of replacing them. But if you know where you can get replacements for cheap then go for it. I rebuild my loose ball headsets about once every two years and even on all-weather commuters (with a front fender) they seem to hold up fine. And if they die, break down and drop $10-15 for a new one.