I notice no cross tolerance from one psilo exposure. The experience tends to be stronger. Ayahuasca with psilocin/psilocybin, with or without DMT, is a deeper more theraputic experience for myself anyway. I prefer to just use rue and mushrooms, and start with the mushrooms. Same goes for rue and LSD.
For multiple nights, either or worked in the past. I have taken mushroom and then aya many times without noticable tolerance.
Good luck!
Long live the unwoke.