I've had boats, big block jet boat... Loved them, used them, sold them.
I bought a 28" camper last year, we plan to use it a few years and sell for maybe half of what we gave new. Call it rent...
I went through the sled pulling thing for almost a decade, sold all of that for ten cents on the dollar rather than store it.
The Jeep is my next loss, I'm around $60k into it, but my interest is fading and it's hard to sell something that's been used in rocks, is highly modified and has dents all over the body and frame. But when I'm done, I'll dump it for whatever.... I spent the money for the fun I had.
Oh, I went through the diesel truck thing back in the mid to late 2000's. I had to have thrown an easy $150k away in that game! Drag racing trucks and blowing up Cummins engines and transmissions gets pricy...
The gun thing... Somehow it made sense to buy 7 AR, 2 AK, 2 SKS, a couple Glocks, a couple M&P pistols, a couple 1911's, a couple tactical shotguns and a couple XDM pistols..... I've not fired a round in at least 5 years now. Oh, and I bought all of that in Democrat scare periods when prices were fabulous for the gun dealers! I haven't sold that pile off yet, but it crosses my mind now and again. What a waste of money sitting in safes....
I also have a dozen or so RC stadium race trucks, I got into racing in the clay stadium tracks for a few years.... So you know me.... I went all in! Those sit on shelves on my basement wall. There has to $25K in RC crap down there, all untouched for years now.
It's not sad though. It's all things I wanted to do, things that I enjoyed and was interested in, and done with money that I had after paying my bills, putting away for retirement and living life with my family. I don't need to be a millionaire at 80 years old. I need to suck in and savor life now while I'm youngish and have the ability to follow my interests... All while ensuring that I'll have a very comfortable and early retirement.
Nope. Not sad at all.