My man lived by the rule "Any fight you can walk away from." He got into a shitton of fights, lost most, went drinking almost every day of his career, and stitched himself up in shady back alleys to catchy music. He lasted 40 days, a little over a tenth of a year, which judging from the other comments is almost a lifetime in this hellhole of a town.
Seriously. Great game, nailed both the atmosphere and the emotion of being the miserable little sheriff in a dead-end horrid little town you'll one day leave in a nice box shaped just for you, assuming you don't get hit by a train, eaten by a bear, or buried in a shallow hole that an anemic, underfed, and grateful vulture will pull bits of you out of later and get drunk off.
(Translation: great game, mostly luck based but survivable with careful resource management. let me know if you ever publish another version :p )