I've been a Leica shooter since the 1970s, so I eagerly anticipated a digital M.
I bought my M8 new, six months after the initial release, once its issues were pretty well understood. No regrets. If I'd waited until it was a "bargain," I'd have missed two years of digital photography with my M lenses. I just don't have time for scanning film anymore, as much as I love the rendition of slide film and "real" B&W. The consolation was that while the M8 had a different look than film, the image quality was actually objectively better.
I preferred 50mm with film. I didn't find the M8 crop factor an issue. In fact, I kind of like the slightly wider "normal" that a 35mm lens provides on the M8. If I were a wide shooter, I might have a different perspective.
I needed a moderate wide for the M8. Since I don't usually shoot 28mm with a full-frame camera, I decided to forgo a Leica lens and picked up two used CV lenses: the Ultron 28/1.9 and the Skopar 28/3.5.
The M8 has been with me on all my vacation trips, and documented my friends and family, and done some "street," available light and classical concerts. Since I rarely shot above ISO 800 with film, I found that I could do everything with the M8 that I could with film, and a bit more.
Yes, I'd like better high ISO, and eventually I'll probably get an M9. But there are plenty of good pictures left in the M8. I've got the lenses I need, I've got the IR filters. There are a few 50mm lenses in my closet that keep whispering to me, Wouldn't you like to use me more? I can be a normal lens again." I'm telling them to be patient, and I'm not selling them.
Like many, I initially came to this forum looking for M8 information, and am happy to have met such nice, knowlegeable and helpful people here. Unlike on some forums, I suspect that the M8 and M9 folks will stay friends!