Hey & welcome! Sorry I missed this thread earlier.

Originally Posted by: rcrousejr

However, I am taking lessons again to challenge myself and would like guidance on the right path to learning how to "groove."

In order to do this you have to have a repertoire (or a vocabulary) of musical things to play. When you see a musician do this sort of thing they are taking all the things (chord progressions & riffs from songs, licks from solos, etc.) they already learned so well it's second nature & reorganizing it in real time.

The trick is that all those physical motions have to be automated to the point at which you don't have to stop to think about every physical motion or detail. Years of repetitious practice turn the motions into "muscle memory" so the conscious mind is free to think in larger units, "I'll play that series of chords next. Now I'll throw in that bluesy pentatonic lick. The next time through I'll play that rock riff with the diads."

So, learn songs, chord progressions, riffs, licks, solos, etc. And practice them until you can do them in your sleep! And then you'll be able to improvise & groove in the manner you described.

If you need help finding specific lessons aimed at your desired playing style & skill level, then please ask! Best of success!