So here is my list. Going from least realistic to very realistic but I have just been lazy to buy/pursue it.
1.) TBM-900
2.) TB-21 (the Mooney was a very close tie here, but can't beat the cabin width of the TB20 series, plus the TBM above borrowed some wing design elements from the Mooney 301 so it's there in spirit)
3.) Modestly well equipped Archer II
4.) An Instrument Rating
5.) A nice goPro AV setup to record my flights and review them to learn from them, etc.
6.) A proper flight bag complete with some survival gear, flashlights, etc. Books I really don't need as they're on iPad
7.) Yoke mount for iPad/FF (I don't really know if I want this... but the iPad is always kind of in the way and I am not a fan of the suction mounts)
8.) Oxymeter (while San Diego itself is not at elevation you need to be able to cruise comfortable around 9K or higher for any real cross countries.. I've never had an issue but this would be a good safety to have)
9.) A full logbook and good stories
And no, I wouldn't want to own more than one plane, unless they were dramatically different (say TBM-900 and something small on floats), in all reality the TBM-900 would come after the sale of the TB-21, and TB-21 after the Archer. Figure that's a good-ish step up plane from simple, to complex, to turbine. And no, I'm not interested in the PC-12. The thing is awesome but I wouldn't buy it for the same reason I wouldn't buy a black Escalade.. at this point PC-12s seem "too corporate" for personal use. And no, I wouldn't want anything bigger.. would still be nice to get into small-ish places off the beaten path