Thankfully I haven' sold anything that I have regretted but in hindsight, there are many that I wish I had of purchased but didn't because I thought things were on the pricey side and would eventually come down.
One that immediately comes to mind was a PSA 10 Sidney Crosby RC that I could have had for $1,000 CDN. A thousand was a thousand and I thought my wife would kill me.
Those cards are currently going for around the $5,000 CDN mark now in a BGS 9.5. and even higher in the PSA 10's.
I also regret, instead of going for 52 commons starting back in 2016, that I didn't grab the highs instead, but who knew?