There are Facebook groups dedicated to finding others. You can apply and cross at any time, but the more in advance you're searching if no other group suits you the higher the chance you won't be alone.
At the end I was in a situation where there were two groups entering at the same time with different agencies. It would have been cheaper per person if that would have been one group, that just happened because everyone first found one of the agencies and then searched for others to join. So plan ahead and find buddies before inquiring!
You can cross any time, I know a French person that crossed Tibet in December. It's cold, but the agency doesn't mind
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