I played the DOS version twice. The first time I got stuck because the version I played was missing some of the vignettes, and the second time I made it all the way through and died in my sleep.
Had the same problem with the one I got off Home of the Underdogs 6 or 7 years ago. There weren't enough squares under 'teenager' to get to the next phase. I fixed this problem by trying to marry my girlfriend over and over again, progressing my age by a couple weeks each time, until I hit young adult.
For the 'too many' vignettes problem, which is common with the browser-based version, because it added more scenarios, I like to look at the squares as a chain or a progression. I go down the lines and whenever there's an intersection, I choose one and can only go back if there's a dead end. That way, I get a fairly realistic aging system. For dating, marriage, purchases, school, etc., I just click over there whenever the mood strikes.
I experimented with scrolling all over and randomly picking stuff I thought I needed, but I ended up stealing a dirt-bike at age 4 and going to juvenile hall. I think a system where it randomly chose squares for you depending on your exact age would be neat.
Does purchasing things even do anything? I always end up getting a really fancy house, but they don't seem to have any discernible effect.