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Started development in 2004, focused later too much on easy money (flipping), should have cloned the success sites instead. Not a big regret though, I enjoyed doing both.
Wasting money on new regs and then falling in love with them over time. The longer you hold on to them, the more you have spent on renewing them so you don't want to let them go... a vicious cycle that drains and ties up your cash.
Also regretting on letting a $200K offer go away because of greed. It was a first offer and I thought I had room to negotiate. It was also one of the first offers I have ever had on a domain name so I let emotion get into it.