Personally, I tend to play some poor guy without any land or family anymore, and who as nothing else to do that to kill himself, or to wander like a ghost (and in M&B there's no suicide… ^^). So they are generally bounty hunters, or celtic liberty (solo) fighters who become gradually either loved or hated by the population and/or some lords… I don't often play enough to rule something but in this mod, it's not very important I think.
By the way, I often just buy no more than one winery, because it gives a REALLY big income and I think it breaks the game somehow to have that great amount of money, no matter what you have to pay for it… Because after buying more than one − at least in my playing style −, you no longer have to watch your money, just like a cheat. And I won't give up trading just because of that, it's a part of the game too. If it's not going to be balanced, maybe could the price be very high (60 000, 75 000) ? Or some enterprises reserved to high renown ?