I've found myself in a similar situation as you. I started playing in a band back at the beginning of the year. I have a kinda hybrid Jerry/Trey rig including a guitar with 3 Humbuckers and the other guitarist and I both have very similar pedal boards, tones, and approaches to playing.
We play mostly classic rock and around 20% Grateful Dead and I decided to take a deeper dive into Bobby's playing in order to distinguish myself from the other guitar (not to mention, he's honestly a better lead player than I am even though we both take leads).
With a little tweaking I'm pretty happy with my "Bobby-ish" tone from my current rig (Mesa Boogie Express 5:25 w/ Tone Tubby 10" speaker). We don't really try to "reproduce" songs, we're much more likely to just take the chords and make a song our own, so I'm not really going for an exact Bobby tone, just something that feels authentic to the music.
That said, I'm going to be hosting a Grateful Dead jam night starting next month, playing the Bobby part, so started researching here on RUKIND. I just took a chance on a JC77 and WOW, I've only started playing with it but it really is everything I hoped for so far. I have an early 80s Hondo II neck-thru guitar that currently has two unknown Dimarzio PUs in it, plan to turn it into a "poor man's cowboy" type guitar, but plugging it straight in the JC77, a bit of chorus, and both Humbuckers is pretty much the tone I'm looking for. Can't wait to play it next week with the band.