Joe,

A hybrid approach to what is pointed out above AND doing what is natural to you - an analytical approach, might work for you.

Part of this is ear training for chord types. For me, I remember that when I started to hear add2 chords in several keyboard parts of Journey songs in the early 80s, I knew I wanted to learn what made 'that sound'. I told my piano teacher and she put me on a serious chord theory diet, tying 'the sound' with the chord structures and inversions.

You can train your ear to identify chords and inversions of chords with enough ear training. If you want to focus on pop songs - do this:

Get a reasonably trustworthy chord chart for 1 song you want to learn. Pick a chart that has more than just the basic chords in it - look for more complicated chords identified.

Play along with it using the chords identified. Get that song down. Then, start messing around by simplifying the chords and listen to how the song becomes more hollow and less interesting, then add the decoration notes back in. Go back and forth with this and your ear will develop the ability to identify the right chords. Find another song with a different feel. Repeat the above.

This worked for me, and I think that you and I share some tendencies in learning style. I've shown this technique to some others in the past while teaching guitar. Some people can't do this - like learning a foreign language, there are some that can't get their voice to take on the natural accent spoken by native speakers. I have a theory that this inability to mimic also ties in with ear-training capability. But I have nothing to go on with that theory, but I have noticed that people that can pull off speaking foreign languages with natural accents also make pretty good ear-training capable musicians.

-Scott