Originally Posted by mrgeeze
From another guitar player:

As far as learning the head, decide whether you're playing single notes or using the guitar's polyphony to create a more complex arrangement.
If its a guitar arrangement then perhaps listen to some of the great guitarists arrangements of the tunes to inspire you.
Perhaps a little of both if you have a band or some backing tracks.

The arrangement is yours and yours alone. Make you part of your work.

On the soloing, personally I find memorization less than compelling. If I want to hear Chet Baker's solo on Autumn Leaves, I just play the record.
That being said an homage to Chet in your solo is definitely cool.
Identify some real "Chet" licks in his solo and reference them in your solo. A difficult one or two is nice to add just to show your chops.
While your adding Chet consider some of the others- maybe even an Eric Clapton lick or a Wes Montgomery octave passage.
Its all legit. Certainly does NOT have to be note for note.

Don't think too hard about it. Just start playing the tune.
Let it come to you. Rubato.
Never play the same thing twice.

Have fun

Such wisdom. Thank you so much I really appreciate the insight!

Jazz hands!