SuperHeroesIncorporated for $5k. At that point, I was a teacher and only had domains so that I could build out little sites for my students in mostly superhero themes, but never considered selling them. $5,000 for paying about 4 years of registration at under $40 total cost made me consider actually trying to sell them.
Ironically I haven't gotten near that much for a hand reg since I started trying to sell them and now don't hand reg much at all.
Just around the 1 year mark. Also sold a name I bought for 12.99 dynadot to the same end-user in the same transaction for another 7k. Total was 14k in the sale.
16k was the last one, ton more all across the board 1k, 3k, 7.5k, etc... My whole business model is hand regged or expired $8 domains into x,xxx-xx,xxx.
Hand regged an expired .co.uk Sep 17, sold at auction yesterday for ยฃ3,805 - could've gotten more if I had waited for the right buyer, but happy with the outcome.