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To me, it depends more which team you like building. Would you rather pour through the draft, and search through prospect lists to find guys that other teams don't want? Or would you rather troll the free agent market, and find players who can provide you returns within your budget.
Personally, I almost prefer losing. Not because I don't like myself, but if I have a top team that I feel should win every year, I get really sad when they don't. And I make irrational choices, with somewhat violent mood swings, trading away a guy who hit .106 in the playoffs, for example. Yes, it's fun in a different way, but in a lot of cases I'd rather play the young team, because you get the fun when your waiver-wire pitcher ends up going 15-10 on the season, and the joy of finally making the playoffs.
Plus I hate overpaying for players, so if I have the veteran team I know I'm going to have to pay more than they're "worth", so I just get annoyed at that.
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