I say it will love of course. One of my best friends of all time is a huge Deadhead....like HUGE. Like growing up if we were in his car that's all we listened to. He'd always be like "Oh, this is 10/9/74 [don't know if that's an actual Dead show]" and then proceed to tell me the highlights of it and where Jerry's guitar solos really tickled your balls. His dad's favorites were Van Morrision, Dylan, and the Dead.
He only listened to the Dead to a fault. If we talked about Hendrix, Zep, etc...he was totally lost. If it wasn't Dead, Jerry, or adjacent then he didn't care. Because of him I saw Phil Lesh and Friends, Ratdog, Dark Star Orchestra, etc. numerous times. It wasn't my thing but he's my boy.
Funny enough, he got into a period of playing the banjo (he got remarkably good, remarkably fast) and completely stopped listening to the Dead. I guess he's got a personality like that. He then became obsessed w/ bluegrass and banjo (but specifically J.D. Crowe).
Then, a couple years ago he kind of put down the banjo and now is back to listening to the Dead without reservation. He bought a bunch of taping equipment and follows around DSO taping their shows.
I'm more or less indifferent to the Dead. Nothing good or bad really to say. I enjoy some of it and will put on their stuff sometimes but wouldn't call myself a fan - maybe a hesitant appreciator.
But let's not fool ourselves....the Dead are decidedly uncool. And that's part of their charm. Because to their fans, they're the coolest thing on this hot planet.