I love it when an old thread gets resurrected.
Having read the whole thread, I confess that over the past forty years I have in fact bought and sold pretty much the same kit now at least three, and maybe four times. And each time it was Leica. And each time it involved one body at a time and at least a 35-50-90 combo. I've had two M3s, an M2, an M4-2, M4, and now an M8, M9, and M4-P with eight lenses and a Visoflex III.
In between and concurrently there have been other systems: Canon EOS film, Hasselblad, Kiev 88CM and Olympus digital (plus a slew of individual bodies and lenses I bought and sold cheaply just because I wanted to play with them to see what they were about.) I also played with FSU rangefinders and lenses, but frankly that was mostly for fun as the bodies are klunky and difficult to use (IMHO.)
And now for why...
The past 40 years in photography have been unlike any other time in its history. From the development of the wet plate to the development of the M4, Hasselblad 500c, Nikon F, and Canon F1 cameras just hadn't changed much. Photography hadn't changed much. Negatives and cameras got smaller and more refined, but the technology remained similar. Pioneering 19th Century wet-plate photographers could have picked up an M4, F, or F-1 and been making images in minutes.
The world changed with the introduction of the Canon EOS 650 in 1987. Electronic cameras took over the world. The computerization of cameras and then digital imaging has turned the world of photography upside down. From the 1970s through the 1990s automation improved and auto features improved so significantly that sometimes auto focus and auto exposure could actually respond faster than I could. I sold my M4-2 kit and bought an EOS1 kit and didn't look back for over ten years.
Around 1998 I got out of the business. I sold my Hassy system. I sold most of my EOS system. I kept one EOS 1 and a couple of lenses. I just wanted a family snapshot maker, and returned to Leica and bought an M4... and the 35-50-90 setup.
Digital made it's debut... and started taking over. I got back into the business with Olympus DSLRs in 2003. I sold the last of the EOS1 gear, but kept my M4. After another year, and now being heavily invested in Olympus digital gear, I knew I'd never use the M4 again, and there was no sign of an affordable digital M on the scene, so I sold the kit. Big mistake as it turned out.
Now, another ten years has passed and digital has matured. Leica is in their third generation of digital. New ancillary technology is emerging. EVFs on mirrorless cameras are becoming the dominant market share. I've found that I don't like EVFs, not at all, and for a variety of reasons. Olympus is going down that mirrorless road now, and I suspect that their next flagship pro model may likely be mirrorless with an EVF. Further, Olympus had dropped most of its pro accessories; flash battery packs and other pro-only gear, so it's likely that their next "Pro" model would be even less "Pro"- oriented than the E-5. So, I was faced with a decision: a) play the waiting game until the current gear I had was hopelessly outdated in the digital world and lose my shirt if I liquidate; or b) stay with Olympus and potentially have to use a body I'll likely detest; or c) just sell it all and get out while the getting was good, my equipment still held value, and the Olympus pro-E line was still static. I chose plan c).
After evaluating all of the choices available and recognizing my life-long comfort with Leica M, re-buying my Leica kit in digital seemed like a reasonable option.
So, here I am again for the third or fourth time. It's like deja-vu all over again... and again... and again. This time, though, I'm a lot more mature, there isn't the market change we had twenty years ago looming on the horizon, and the technology has matured. I think I'm here to stay.