Oddly the gear I have the most emotional connection to is not the best gear.
My H/K 330c has been a constant companion for something like 23 years now. I was dumb when I got it, there's a mark on the face where I straightened it with a pair of pliers. I "fixed" some scratchy controls back in the day by dousing the pots in WD-40. I know better now, and I have better gear now, but someday I will fix/restore it.
Other gear I have an affinity for:
Pioneer PD-M910. yeah, it's a damn CD player. Other than the Burr-Brown DACs there's nothing about it that hasn't been eclipsed by more modern stuff. It won't play SACD, DVD-A, or even decode HDCD. But it has freakin' rosewood veneer side panels, and pop the top on it and you realize that it was Pioneer's best effort back when it was built to make a truly top shelf unit. Yeah, it's a changer but it has a damn COPPER CHASSIS. I could just go get a gently used Oppo 105 which would do so much more but it's kind of cool to have the SOTA of back in the day.
Sansui QRX-7001: this guy does everything. Swiss Army knife of 70s receivers. And it looks cool too. Someday I will get a 9001 and hate my life as I pin all the pass throughs.
Luxman R-1120: this is a love hate relationship. It's broken. Again. But again, SOTA for the time, at least as far as receivers go..
AR XA: it's a (expletive deleted) icon. This one isn't a love/hate, it's mostly love, but it does require a solid stand.
Technics SL-1650: see AR XA supra. No, it's not a SL-1200 Mk2 but it shares a lot of genes with the Mk1 and it's rock (expletive deleted) solid. Definitely a milestone in Technics history.
I guess what I like about gear, secondary to the intrinsic "it sounds good" quality, is historical significance and/or that said gear was at/near top shelf status when it was made and shows the pride of the designers, and even if it has a mass market brand name was still their "statement piece" if you will.
Now here's the funny thing - the best gear I have sonically is probably my H/K 700 series stack. But it's all silver colored plastic and it doesn't near inspire affection from me as much as, say, the broken Scott 340B that I will restore someday, I promise. Something about real wood and aluminum that makes me overlook sonic deficiencies, although I can't say how big they are as I've never actually listened to said Scott.
No, I don't have any McIntosh, Phase Linear, Accuphase etc, gear... yet...