There are two routes to the top of Masada - the Snake Path or the Roman Ramp (with stairs at the end as it never reached the very top). I've taken both and I'd recommend that you need walking boots but you don't have to pull yourself up. Make sure you have water on you as you will be extremely dehydrated if you don't drink on the way up, there are water drinking cisterns on the top where you can refill a bottle but none on the way up.
I have done it twice. Only take the snake path, wear good tennis or hiking shoes, Take plenty of water go early in the morning and enjoy the sun rising ENJOY