I have done 96 trips for myself and family almost all in International J.
I have booked about 50 more, but had to change the dates and details or cancel due to no leave being available.

I think 1 trip was a domestic y in 1991.
2 more were Int Y to greece in 93.
None in Y since.

Hotels only a few. I transfer all my miles to airlines.
I did manage Hilton Copenhagen Airport
Highly recommended for location and ease the night before the SK flight.

I haven't been keeping track but I am sure I have over 100 free flights. Just this year and just to Alaska I have booked seven flights for friends, family and myself. And in 2006 I booked another 7 free flights just to Alaska. And I have used miles to a lot more places than just Alaska. Have three biz tickets booked for 2 friends and me to Europe for next April.

Won't get anywhere near 100 free hotel or car rental days but I use my points for high-yield flights.

I would have thought that:

Triple = Top elite status on 3 different airlines within the same alliance
Triple Triple = Repeat the same to all three main alliances (OW / *A / ST)

That's a good alternative. I don't think anyone has qualified for your triple/triple either.

I constructed my scale to resemble the triple double in basketball, so I didn't think about elite membership as a qualification.

The 100 or more free car rental days were going to be the hard one in my scale. From the responses only one member thinks they had over 100 free car award days. I was surprised when that member missed on free flights. So nobody has made it so far.

If I changed car days to free status driven flight upgrades then I think we would have quite a few qualify. I have had about 75 segments upgraded on Delta because of status. So I would still miss my triplle/triple. But I still love the free stuff anyway.

It makes for a great vacation when you fly free first class, stay in a high end hotel free of charge, and have a free car at your disposal.