I'm not expert, but the biggest thing I've found with choosing roles is to figure out the consequences of other people choosing them and you not getting them.
Captain: Look at what goods everyone has and who will benefit most from picking it. If you forgo the captain and the next person takes it, how large will the change in your victory points be? If you're both sitting on 5 barrels of corn, you want to make sure you load first, because otherwise you probably won't get to load much and may even face heavy spoilage. Like Mr. Roberts said, also look at forcing other players to ship goods they'd rather trade, like coffee and tobacco.
Trader: Look at who has what to sell. If you can get some nice cash by selling tobacco or coffee AND screw over anyone else who might want to sell that too, then this is probably a good choice. (presuming they don't have an office, in which case it won't make a difference)
Mayor: Look at how many colonists the picker of the mayor gets vs. everybody else. If the number of colonists on the colonist ship is the same as the number of players, picking the mayor will give you only a 1 colonist bonus over everyone else. If there's more, you may be looking at a 2 colonist bonus over the player to your right, making it more attractive for you. Also consider what things are on your island you want to get into operation as soon as possible so you can use them in the appropriate phase.
Craftsman and Builder: Unless there's a shortage of goods or desirable buildings, I often try to make other people pick these as the bonus for doing so is fairly small. Getting goods or buildings doesn't matter much, usually what's important is who gets to use them, which involves picking other roles. Are you setting up the next person for an amazing captain or trader phase by producing now? Can you earn the 1 doubloon bonus from picking the builder some other way? As I said, if you really need the advantage of producing first or building first, that changes things.
Settler: Look at the available plantations and who would get what. If you really want one of the plantations and there's only one of it, chances are you won't get it if you don't pick settler yourself. If you don't plan on building a construction hut and want some quarries (which are always awesome to have), the only way you're going to get them is if you pick the settlers.
Obviously there are a few other factors that come into play, the biggest being the amount of doubloon on each different role, but I think its affects are pretty self-explanatory, with the same ideas of trying to get the best advantage possible while denying other players the optimal choices. Number of players, buildings and plantations on your and other players' islands, position of the governor marker, number of each plantation and building left in the supply, and time 'til endgame all come into play as well, but to keep this post from getting to long I'll omit those for now. :D
So what can be done in reasonable amounts of time?
If time is a constraint, just try not to think too deeply. Its very easy to spend 5 minutes analyzing every possible move and consequence as all hardcore PR players know. Just look at your options, figure out the pros and cons, keep your future turn simulations short, and try not to second and third guess yourself. When in doubt, go with your gut.
Are there any kind of tools to help training this aside from full games?
Not specifically for PR that I know of, but if you find anything I'd be very interested in hearing about it. :D