Oh yeah, I have had buyer's remorse several times. I had my nicest camera equipment when I was still unmarried, and was living off a very nice scholarship and teaching-assistantship in grad school. Everything was paid for, and I remember buying loads of equipment, trying it, sniffing that it wasn't good enough-- it wasn't me, it was the equipment's fault-- and sending it off, usually with a small loss/gain. This was around 2003.
At that time, I had bought a new 35/1.4 ASPH for $1300, which was the going rate at the time. It was my first 35mm focal length lens-- I had just used 50s. I took it out for a couple of rolls and said to myself, "I don't like it". I sold it to a Photonet Leica forum guy who still posts there; I hope it's doing well. I regret selling it because it's one of the 'grails', though when I think about it more, I don't because 35 has never been a length I like.
Now, the equipment that really sucked to sell: fast forward 2.5 years later; the scholarships have dried up; I've gone overtime with my master's degree; the thesis is 0.5y late. I needed to sell something to pay for my tuition fees. I had a Plaubel Makina 67 that was in excellent condition, that I had picked up for $600 because the seller had said that sometimes, it didn't wind (never had a problem with it). I sold it for twice that amount, and that just covered tuition. I miss that 6x7 negative and the 2.8 lens! And now, 67s in good shape are over $2000.
So, you can buy the gear again, if you put that to be one of your priorities. I'm a family man now; I have a wife and child, and a house; there are many people and other things that come before gear now.
But that M4-P is still there... and a KEH bargain Canon 50/1.4 LTM is on its way in the mail... the flame still flickers!