I had curated perfect-to-me PS1 and PS2 game collections, and had the later, smaller versions of both systems. Both whole collections fit in a bread box, but I gave both away to save space. I cannot believe how much I regret that.
I have the same regret, I gave my N64 to a family friend in the late 90s. However, I later bouught a replacement N64 with two new-in-box gold controllers so I can still get my GoldenEye fix.
Not a console but I used to have a working Amiga 500 in the 90’s which I got rid of in favor of a PC. Wish I’d had held on to that one.
Never personally sold any of my previously owned consoles, but I did “lose”* my Super Nintendo around 2001 and, sometime in 2011, my older brother messed up my PSone’s lid and it “disappeared” shortly afterwards.
* This loss was either my mom or aunt getting rid of it because "nobody is using it anymore, it's just wasting space and gathering dust". The same end my brother's CCE Turbo Game (a brazilian famiclone) had when I was even younger
I’ve been feeling this lately as well. I’ll see people post pictures of display cases filled with all their consoles and it makes me regret giving away my old consoles when I bought a new one.
I especially miss my N64.