My parents used to live up on a mountaintop in Boulder, Colorado. The elevation where they were at was close to 9,500 ft MSL. It would take a few days at least for me to adjust going out there as I live in St. Louis, Missouri, in an area only about 450 to 500 ft MSL on average. After you get used to it, which to fully do can take considerably longer than a few days, it's easily tollerated.
I would be wary of flying without O2 up there even if under 12,500 though for any length of time. It certainlay can't hurt to have supplemental oxygen on when at an altitude significantly higher than what one is used to normally.
I've also been in an unpressurized aircraft as a passenger at 13,000 feet MSL on one occassion. It was not a pleasant experience! You know how the FAA rules read that the pilot has to have oxygen, but no real requirement for the passengers is there if you're below 14,000? Granted, the FAA wants to make sure the pilot can fly the plane properly.... but they obviously don't care if your passengers are literally blue in the face
I guess the old saying is true about the FAA...."We're not happy until you're not happy!"