I would find that my biggest downfall is patience with the process of making cash in order to set up my growth.
I'd begin by recruiting a small force and heading for the sea raiders. After only a few fights I'd be rather wounded and would have to skulk off to a town in order to safely heal up before trying to replace the manpower losses from the fights and then head out to do it all over again. This certainly ended up being nice when I could score some equipment upgrades and not appear like I was wearing a Target brand fur lined coat. The problem with this would quickly become difficulty in finding sea raider parties in general, let alone parties of a size that I could handle.
...So I'd inevitably turn on the cheat to show all troop movement on the land in order to spot those gruff sounding sea raiders. Cool, I know exactly where to go to find a fight, but after another hour of this I'd begin to get bored with the process and want to try something else... Like tournaments!
Who doesnt want to stand on a tourney field, with their arm held high, in stunning 8bit glory? Okay, 'tis better than 8bit glory but my intentions were pure. Find a city with a tourney happening - save the game - and enter, betting 500 denars on myself each round. 4 rounds later, scream in "archer vs mounted knight" frustration and reload. Rinse and repeat. Several bottles of beer and several reloads later I have won the tourney, along with a nice cash prize. Dedicate the tourney to the lady present whom happens to catch my eye and hunt up the next tourney.
Do this several times and suddenly there are no tourneys left. Check my funds and I've certainly got enough to begin several enterprises, but I'd find I'm needing to quickly get back out there to make more money. This fighting thing seems to be working well, but hang on - I was developing a character with skills invested in trading and party size management.. So my continued fighting is going to be crap unless I alter the design or just go ahead with the party.
Quick decision made, I go with a mass recruitment spree in order to get in on bigger fights ( bigger fights means more loot, means more cash... right? ...huh? ..right? ) and way I go, off to sign on for some merc work... Only to find I've not got the martial skills, nor party size to really stand up to the enemies of my new lord.
Do your trading, fight sea raiders, fight bandits, loot the occasional out of the way village. Build up an enterprise in every city if possible. Enter into tourneys. But do it all with patience, young padawan.
