I've also thought at some points that the game could use more tooltips for certain mechanics, and some order in the skill list could also help, perhaps. The real question is, how far do you want to take it? What sort of tooltip is appropriate and what sort of tooltip caters to the .. well, i wanna say drooling idiots, but it's more a case of lazy gamers, that need to be spoonfed the info otherwise they turn the parody "How maek fire" into reality. Do we really want this sort of behaviour to be common?
https://www.youtube.com/watch?v=MS6m2A_3V04Anyway, the type of tooltips I'm thinking of are more .. ones that make your curiosity peak and make you want to explore, which is the general idea of salem anyway. JC tries extra hard to make us all figure stuff out as it gets implemented, so to think that he would swich that philosophy to outright adding turtles with the tooltip
"The hare's laziness lost him the race, but he needed only to wait 3 more years and that turtle ***** would die of old age, and then he'd be the fastest critter alive!".
I just can't see such outright freedom of information actually happening, and I can't say i'd even like to see it happening. The one thing that needs to be kept in mind is not penalizing noobs too harshly for being real, off the boat noobs to the game. Not fresh chars, but totally new to the whole concept. In that sense there's been a lot of input by the community about how to make the newbies live through the colder winters, and past that a few tooltips would do wonders for 'em. Hypothermia itself having a tooltip that says "Brrr I need to craft some more clothes, it's getting chilly" or something.
In terms of the skills being split into trees, I guess that could be done. Make sections for skills of the same category. Tailoring skills in a category that says "For the aspiring tailor" or the combat skills in a category with a tooltip "Durid is 4 fite". Tho as it is the skills' tooltips perhaps do decently to describe what stuff does. Some error messages could also include hints as to what you need to do to progress. Try to attack a cricket without bug hunting, get an error message saying "You flop around like a limp noodle in the wind, if only you'd learnt bug hunting you wouldn't suck so hard" >.>
As a final thought, my tooltip ideas need to be a lot shorter sentences xD