I restrung my Les Paul. With a Bigsby. Even with two capos and the tool kit my Telecaster came with, which includes a string winder, it was a pain.
For those not in the know, Bigsby vibratos have these little pins the ball end of the string is supposed to hang on to. Pre bending the end of the string does not help much, so I used one capo to keep tension on it. And another capo at the nut end to keep tension on the tuner so it winds cleanly.
Even though I bought it new, Sam Ash had for some reason replaced the strings with cheap D’Addario strings that were too heavy, starting to corrode, and sloppily wound around the tuner. Plus the multicolored D’Addario ends look nasty and make it look like you can’t tell the strings apart.