Hi Matt and welcome to the forum! Looks like you've had an extensive collection of guitars over the years. You mentioned playing in an orchestra setting. Did you play guitar with an orchestra accompaniment or play a different instrument?
Too many guitars. Need to make up my mind! But I have gained a lot of experience with different brands, from Ovation (had quite a few including some Adamas) to Martins, Larrivees, Breedloves, taks, and of course Taylors.
I play guitar in an orchestra setting. Think the key of Eb. Needless to say, my barre chord skills have improved greatly. I also have learned to tune down 1/2 step and play in E and if a song is actually in a guitar friendly key, I capo 1.