1. What jacket / pant size do you typically wear? Thinking if there's not more than say an 8 inch drop between them, you might have some luck with scoring a deal off the rack depending on your budget.
2. What sort of budget do you have in mind for these suits? I agree with quality over quantity to a certain point. If you're asking about four $1,000 suits vs. two $2,000 suits, I'd go with the four $1,000 suits. If we're talking $1,000 vs. $500, I'd go with the two $1,000 suits. For $1,000, you can get a suit by www.mytailor.com
(personally, I've had good experiences with Joe Hemrajani there).
3. Make sure you budget for shoes. Allen Edmonds Park Avenues should do the track and will go fine with a suit. If you want to get something a bit nicer, perhaps something from Crockett and Jones. There's other makers out there so don't let this be an exhaustive list, a good suit is instantly destroyed if paired with crappy shoes.