If you had 4500/444s, it would run at max pressure for a LONG time ... slowly eating bearings and bearing surfaces in the process. About 80% of the wear comes in the top 10% of the pressure range so minimizing the time at the highest pressure will greatly extend the life of the compressor.
I would go with the 220 VAC machine with automatic drains.
rcontrera - I have a bank of four 4500/444's and usually top them off to 4600-ish. After reading this, I suppose I should just bank b/t 4000 - 4200. While I have a few HP tanks that I ocassionally fill, I usually fill my LP's (to about 3200).
OP, If you don't plan on taking the compressor on the road, I would go w/ the electric version just for the auto-drain (and it's quieter if you have grumpy neighbors). It's a pain in the butt to have to manually drain the system every 15-20 min or so....