By way of advice for the original poster, you should specialize to a degree, but you have to spread points to some extent too.
The reason is that you need to vary the jobs you're doing. Your motivation has a huge affect on pay, experience, and finding extras. In order to maximize that stuff you need to rotate through different jobs, to keep the motivation level high on each.
You'll also notice <see
http://www.weststats.com/Jobs/> that the skills required for successively better jobs don't flow sequentially, but are interlocking. In other words, when you're doing one job --and have put points into those required skills --you'll likely find that the next job you want requires some other skill in which you've got minimal points.
I would suggest this: use the extra clothes, etc, as your initial guide. That is, if you've got a pair of shoes that adds 5 points to swimming or whatever, then look at the website above and think about some jobs that would make the most of your awesome new shoes/swimming ability.
Try to map out a sequence of jobs over the next 5 levels or so, such that you (1) maximize the impact of the extras that you find or earn, and (2) keep a couple of different jobs available as you move up the chain, to keep motivation high on each one. Then build the skill to get to the next job you want, then the one after...
Essentially, build in a few areas as you go, do jobs that seem most lucrative (or best satisfy your western fantasy life), and be willing to follow your luck.
Good luck, pardner.
-Joe
