cheap stuff is MORE fun because you can do crazy **** on it and not worry too much.
the steamroller is a great bike but deep v's are very expensive for not much return cept style.
it's your first bike. don't worry about getting the most performance you can. a fast bike is only going to make you spend more time to get in shape. pushing a 14lbs bike 100 miles is going to burn less calories than pushing a 25lbs bike that far.
you will NEVER make money putting money into a bike, even if it's a concept. resale value is not really an issue.
get a dawes sst or a schwin madison, as they already have brakes and a freewheel which you will need.
devote at least 4 hours a week to pushing it as far as you can.
get it fit properly by a professional unless you are sure you can fit it properly yourself. you don't want to blow out your knees trying to drop twenty pounds. the 350 could be better spent at a gym that will supervise you in that case.