Leica Ms. Two different M7s, and their accompanying lenses. A several year period of experimenting that left me much poorer and gave me virtually nothing in terms of results. I wanted to like shooting with it more than it actually suited me. I would have made more and better photographs with a cheap AF SLR like a Nikon F80.
Everything else i owned served its purpose for whatever period, and even if i moved on from it, i don't recall feeling real disappointment. Plus, the cost wouldn't have been so high, so a 'mistake' in those areas would have been less impactful. The benefit of Leicas, though, is that you can get your money back out of them. But, not the time or missed opportunities.