The Tele does seem more reasonnably priced, but I'm also a huge fan, especially of Bob Dylan. I actually named my son Dylan after him.
I'm also a huge Beatles fan, and the autographs of the 2 Beatles that passed away surely add value. However, appart from being George Harrison's first electric guitar it was not part of anything major in history; I have never seen a picture of George with it (even from the Quarrymen era) and in interviews he always talks about his actual first guitar: an acoustic that his mom bought for him. Regardless of the condition, it's great that it survived. If someone's willing to pay, then it's not too expensive.
It's hard to tell with collectibles, you never know how crazy the interest will be. Kirk Hammett paid $2M for Peter Green's 1959 Les Paul and he plays it at every concert. I looked into it and found a very interesting list of The 60 most valuable guitars ever sold at auction. I wanted to list a few, but you should really check it out as they are all really interesting and it turned out to be a great read; I couldn't even pick just a handful to list here. Out of 60, only the top 27 fetched more than $300,000. The "cheaper" ones include John Lennon's first guitar, a few of Clapton's, Jimi's Strat from Monterey, the first Les Paul (owned by Les Paul), a few of Jerry Garcia's most famous guitars, Elvis' guitar between 1954 and 1956 (the Sun sessions), Hank Williams' main guitar and much more.
Wow sorry for the long response, but thanks for making me wonder how much it might actually be worth, that list was really interesting.