I tend to keep things fairly simple; I have a rather-constrained library of chords that I use to work out chord-melody arrangements.
These are mostly 4-5 string shapes with the roots on one or other of the bass strings.
Joe Pass, in a video lesson on this style of playing, said "Figure out the melody and find chords that sound good". Pretty much what I try to emulate.
The Jazz Guitar Forum site:
http://www.jazzguitar.be/forum/
Has a wide variety of free lessons on all manner of things including commonly-used chord shapes and progressions... Some very knowledgeable folks there. In addition, the guy that runs the place has a video blog on Tumblr.
I know many think of Ted Greene as the great authority on the subject and recommend his "chord chemistry" books.
But at my age, I find many of his chord shapes quite unplayable. And listening to him play various tunes on YouTube.. Not my cup of tea.