Jeffrey,
I haven't tried, but I think you could win if you put the extra points into the proper areas. For instance, if your fundraising ability is high, this can overcome the low money problem. Low experience is easily overcome by increasing other attributes and playing to those attributes. Low stamina is a hard one to overcome though.
I imagine that it would be a very tactical game. Without the stamina to run around the country and do all you want to do, you have to pick your states and win them with the least amount of effort. For instance, every speech and ad would be important. You probably can't win on the top issue, but you could make a good run at issues 2-5. You probably can't afford to get more than one or two endorsements.
This would be one of those cool puzzles, like the Magic: The Gathering puzzles (if anyone remembers those). Given a particular character, plot a campaign that would win, or at least not lose by a landslide.
Joe