I first got started in Paulsons, with Classics and Pharaoh's. I sold my classics pretty quick. No regret there, whatsoever.
The Pharaoh's, not the same feeling. I was sad to sell it Infact. While packing it up, I was definitely feeling I've made a bad mistake. Never even felted it. Was painful and expensive to build. It needed to be sold at the time, to make way for an AS Hot Stamps set.
That said, I recently bought the whole thing back in one shot. What a great feeling. Now COVID is the only thing preventing me from finally using it.
I also LOVE Jack chips. Maybe it's obvious, I don't know, but I regret selling mint Jack $5s. I had 2 racks. Let them go. Who knows why!!! I've spent months to get them back for more money, by the barrel, and just plain difficult with the amount of shipping and overhead added to get them back. It was one of my more idiotic sales given how much I LOVE the chips and still do. Now I've got 300 just to be sure I'm happy. I desire a 4th rack, but I'll wait patiently or maybe never acquire it, I'm happy and whole again .
Surprisingly, I spent alot of time and money accumulating Blue Chip Casino fracs. Almost 194 of them. I recently sold these. Lost some money. Have no regrets. Glad they are gone and not wasting space in my chip case. I've acquired much better chips that can and will see use in their stead. Can't wait to get them as they are in transit. In this case, this was a solid chipping move and made my collection better. No point in having chips with no purpose past being in a case.