I started domaining around November 2001 and basically hand registered complete rubbish for the first six months! But I still have one of the names even today - 00uk.com !
However I did manage to get a couple of names that were slightly better than rubbish - there were no companies around then that were jumping on names the millisecond they expired!
I sold my first name - CharityAngels.com - in June 2002, turning $30 into $191.90 after expenses - it went to a school in Florida that was doing a class project. (I ended up hand registering this name again later on, and sold it a second time in 2010.)
The second sale did not come until November 2002 when I sold NE1.net, turning $152.50 into $384.10 after expenses.
Beginning in April 2003 I started selling mostly hand registered names on the forums and I managed to sell 122 names in 2003, mostly two word exact match dot coms or one word dot nets / dot orgs. Sales were mostly $xx and profits were relatively thin but occasionally I got lucky and got a $xxx sale. My first low $x,xxx sale was in September 2003 when I sold AtAuction.com. Most of the profits got ploughed back into further names.
In 2004 I sold 92 names, again mostly on the forums but I now started to get a few end user sales, with DrugCode.com, BoatSurvey.com and CowboyLiving.com being the best.
This was the year that I started to get CCC.com names (mostly LLN - where LL spelt an international country code - eg ZA = South Africa; or LNN) and I ended up with over 70 of them. I even managed to get a group of three of them - A77.com, B77.com and R77.com - on Ebay for $43 ! Over the years many of these CCC names have been sold but I still have 29 left.
Most of the names I got for many years were from the closeout section of Godaddy. Many days I would very quickly scan through up to sometimes 10,000 names in a day across the internet, to try and find possibly one diamond in the rough that I thought had value.
Of course on the other side there were hundreds of names over the years that I thought had value but came to nothing and I let them expire. Looking back some of them were awful but some of them were not that bad - I simply didn't have enough patience then!
As the years passed I sold less and less names on the forums and more and more of the sales were to end users, particularly as they were now starting to contact me. Numbers of names sold were dramatically down but the value of each sale was much better.
Giving good service to the buyer and making the sale process as easy as possible was very important to me and resulted in some buyers coming back for multiple names in the same industry. I sold names across all sorts of business niches including for example - candles, white water rafting, heating boilers, envelopes, cars, shipping, boats, cranes.
Today I have quite a lot of geo dot com names (eg Sunderland Plumber, Leeds Legal, London Arbitration, Durham Joinery), quite a lot of two word exact match dot com names, some one word dot orgs from a long time ago, and some one word / LLL / very short .co.uk / .uk names.
In the main I have tended to keep away from the new tld's and various fads in names that have come and gone, mainly concentrating on two word exact match names that can provide value to a business, so that they get more in use value than I get from them in cash value.
I have made tons of mistakes, hopefully learnt from the majority of them and not repeated them too many times!
Patience is an absolute necessity to learn, as is not being too greedy. I almost certainly have not have taken anywhere near the last dollar off the table, but if you get what you are happy with, then go with that and reinvest in a better name. Let the buyer use their expertise to get their share of any remaining profit available. There have been times when I have been on the other side and got a name ridiculously cheap, maybe because I was in a better position to appreciate its true value.
Don't wait for the one name jackpot value sale - it will never come. A steady stream of lower value sales means you create your own far bigger jackpot for yourself!