Tube rolling sounds like a pretty intense undertaking.
Hey if you can tip cows over at night, then tube rolling ought'a be a breeze! No meadow muffins to look out for either!
Because you are talking about a headphone amp that will likely use only a few, smaller tubes, you may be making it seem more complex and expensive than it actually is. Headphone amps are mostly auto-biasing so you don't have to worry about constantly adjusting the bias. With a tube amp it is basically a plug-and-play scenario with swapping the tubes. As Swampwalker indicated, some of the NOS tube prices are as out-of-hand as real estate in Manhattan. But you really don't need to go there to get satisfaction and great results from trying different brands of tubes. Once you choose and amp and are familiar with the tubes it uses, just do some reasearch here and on other Internet forums as to what others with the same amp have preferred. There are a few really excellent sources of new and NOS tubes to consult as well (The Tube Store, Vintage Tube Services, VTV, Upscale Audio, to name a few). You don't have to spend a fortune on NOS tubes - there are current production tubes that arguably have the potential to perform just as well if not better. Anyway, just don't rule it out...on a headphone amp it's no big deal.
Marco