Back when cash flow was tight I always regretted selling one thing to help buy another. I did that with my C64 to get an A500 in the '80s. Whilst I did that through the '90s with some of my Macs, I never was in the position to need to sell my Amiga computers. I did repurchase a C64 later on to alleviate the guilt I felt.
I Frankensteined my original A1200 from 1993 until it was unrecognisable (tower w/ BlizzardPPC and Bvision + SCSI II and a bunch of other extenders) until one day in 2002 something blew. It had a good run. I don't regret selling the Bvision, that was the buggiest RTG card ever made, but I do regret selling the BlizzardPPC, because more than a decade after I originally purchased it they finally released AmigaOS 4 for Classic. I really can't justify buying it again with some of the prices people are asking for on Ebay.
I still have a couple of A1200s and my CD32 with SX1. I am never selling those. Even if I end up being homeless and I am living under a bridge. My...precious.