discussing the merits of those suits is a bit like debating if a lexus is better than a bmw or an audi vs an acura. the tie-breaker becomes the test drive - especially when you live walking distance away.
since this is essentially your first real suit, i would suggest:
1. can't go wrong with brooks golden fleece (fully canvassed and brooks has been having 20% - 25% sale periodically. with opening a credit card, that's another 15% off if you wish). my personal experience with their MTM line is that it's not cost-effective. it does adjust 1/8 of an inch here and there but for a much higher price, and it depends heavily on your body habitus. all their MTM is along the 1818 line. i wouldn't consider brookscool at all. not for your first suit anyway. it takes them about 2 weeks for basic tailoring but i'm sure you can squeeze a few days out of it. alternatively, if budget is an issue, i don't think it's a crime to get an 1818 as your first suit.
2. you can't go wrong with paul stuart either, although PS is a notch higher at least in terms of pricing. if your budget only allows a low end PS, i'd rather go with a golden fleece.
3. I particularly favor ralph lauren black label but they usually start at around 2g and sales have been hit and miss (25% off a few days ago). if you have a buddy that works for the corporate then you can get a 50% off. they're appropriately progressive and sharp but not as aggressive as suitsupply.
4. H.Freeman confuses me since they have too many lines at too many different stores.
5. j press is down right too conservative.
finally - keep it simple. having too many choices for your first suit CAN confuse you . you are not expected to get it perfectly right the first time around anyway. good luck with the girl - i'm sure she will be far more impressed by your generosity to the charity and your gentlemanly sincerity than whatever suit you choose to wear.