I pulled the trigger on an $8300 pinball machine almost four years ago and have never regretted it. I play it at least once a week and it’s the centerpiece of a monthly happy hour we throw once a month. It doesn’t hurt that I can still sell it for more than I paid.
Oh, that brings up one I hadn’t thought of. A few years ago I built an outdoor all adobe and stucco kiva (like a southwestern outdoor fireplace). Wasn’t really ‘big-ticket’ (I think it cost me around $10K), but I love the thing and in the winter I spend most weekends outside with a nice fire, a cigar and a bottle of good tequila, kicking back and relaxing.
I’m not sure my bigger expenditures were my more satisfying.
The single purchase that gave me the most satisfaction was a 62 Corsair in 09-ish. Unfortunately, my wife hated it and I eventually sold it. But the car only cost $2500.
I had a nice upright bass custom built. I get a lot of joy out of playing it. Tho for many uses, I prefer my cheap ld plywood bass.
When we redid our current house we splurged on a brick driveway. It was stupid expensive and ridiculously impractical compared to concrete or asphalt, but I regularly think of how much I like the looks of it.
A couple of years ago or so I dropped almost two large for 3 premium seat Hamilton tickets at a time when you just couldn’t get any tickets. My SiL desperately wanted to see it, so I treated her, my brother and, of course, myself.
Needed to get a new toilet so I splurged on one with heated seats and integrated bidet. One of the best purchases I’ve ever made.
On the vacation side of things, for our 10th anniversary we booked a trip we really couldn’t afford to a tiny private island in the British Virgin Islands. The place is amazing, just a handful of guests at any one time, great food and accommodations without being overly snooty, and just relaxing and private as all get out.
A new Google Pixel phone for $400. Rs an older model, a 4A 5G, now discontinued, but it does have 5G, and around 5Gb of RAM, so it’s super smooth and super fast. It also has Android 12, so it has a lot of good features, such as call screening and real-time captioning on calls. I can even be put on hold and have the phone notify me when the caller is back on the line, so I can set the phone down and do something else. The battery life is good, too. I was getting tired of buying cheaper phones and having to replace them because the battery would no longer hold a charge.
That reminds me, we had a high-efficiency wood-burning fireplace insert installed years ago, and it along with some nice stonework we had done around the fireplace, and a wooden mantelpiece on top that I built, cost around $5K, and I’ve said it’s about the best 5K I ever spent. It heats the entire house in winter and makes Michigan winters much more bearable.
After the first couple years of buying cordwood, I discovered I could get free firewood from Craigslist, so for awhile I was gathering, splitting and stacking my own firewood. It was a satisfying experience. Thoreau said wood warms you twice, when you split it and when you burn it, but it’s actually 3 times-- he forgot hauling it around from point A to point B. It’s a good feeling burning wood you gathered yourself and thinking “ahhhh…free heat!”. I’m getting a little old for all that work though, so after I run out of wood from a big maple that fell on my property a couple years ago I’ll probably go back to buying it by the cord and having it delivered.
Luckily my wife enjoys the boat as much as I do, maybe more.
Prior boats had rugs (mats?) that got gross. The new one is just fiberglass deck and easy to hose down (the boat even has a freshwater hose) The dirty dog isn’t an issue. (We just need to find a way to hose down the floors in our home, because that’s where the big dog problem usually is)
After years of struggling with cheap bike racks with straps and clamps and speed limits and fiddly crap I finally splurged and bought one from 1up-usa .com.
The rack comes fully assembled; open the box, unfold the arms, and stick it in the hitch … done.
It literally takes me 12 seconds to load the bike onto the rack, ready to drive away. It’s been on my car for eight years now and still looks brand new. Best thing I ever bought; no gotchas, no I wish it was, no fiddly bits, no maximum recommended speed.
The only problem with them is they are meant to drive fast. The rear spoiler is actually functional and holds you to the ground like glue. I once drove from Denver to Flathead Lake, MT and averaged just over 100 mph. It felt like I was driving 60.
It never was my daily driver though I had just over 10k miles on it when I sold it 5 years later because I needed something more sensible for my first kid. The '73 CJ5 that was my daily driver didn’t have any safety devices but I couldn’t sell it for enough to buy a modern family car. We ended up getting a grand Cherokee
My wife has promised me I get to buy another one on the other side of kids either that or a late 90s viper convertible
2 come to mind. First was a trip to New Zealand with my wife. We were there for 17 days, 8 of those days were driving around the South Island. A truly amazing experience.
The second was a $350 bottle of whiskey. It normally sells for around $600 in liquor stores and $500 at the distillery. At the time I had a blog and rated made in Washington liquors. I had rated this distillery’s base whiskey, in my comments I mentioned I would like to try some of their Mizunara Oak cask aged whiskey. Mizunara oak casks are made in Japan and very few are exported. A few days later I got an email from the distillery asking me to stop by and try the whiskey. While very much enjoying my sample, the owner asked if I would like to buy a bottle at a discount. I said sure and the rest is history. It is my first Friday of each month dram, sadly I only have enough for about 3 more drinks. It has been worth every penny.
Sooo…what’s that about a problem, then? 
Sounds like a another satisfying and sensible purchase for you would be a radar detector!
The farm. All the things I wished I could do but couldn’t, or couldn’t do well, I can do here. Best thing that ever happened to me except my marriage and the birth of my daughter.
I only got 1 ticket in that car when I owned it. I passed a car that was doing 45 in a 55 but I was doing 100 by the time I drove that car length. Instead of breaking when I got in front of him I took my foot off the gas. Several miles later I coasted past a cop and got a ticket for doing 65 in a 55.
The 470 ftlbs of toque is more fun then the top speed and one of the reasons I’m looking forward to getting that hummer EV next year with its 620 ftlbs.
One I my first dates with my wife we drove the million dollar highway and I pulled 0.8 Gs multiple times through the curves. She squeeled the whole time.
Like I said, I can go on and on about that car.
a roadster that’s fun as 'ell to drive (for part of the year) but totally impractical.
My home office.
Two teenage kids, a wife and me, all trying to work at home and find space to spread out was pretty draining.
Not having the luxury of a large house I decided to spec-up my own bespoke office, working with an online company. Thick logs, double glazed, fully insulated and pressure-treated with electrics and heating. It is only 9 foot by 6 foot but two/three people can work in it comfortably and I have two workstations with two laptops, a monitor, a 42" TV on the wall, some nice Ruark speakers, a Nintendo switch dock and a 3d printer (and it still feels huge inside!). I’m sitting in it now and the wind is howling, the rain is pouring and it is about 5C outside but it is lovely and warm and dry in here. One of the best purchases I’ve made.
All-in, including all structural elements, insulation, treatments, delivery and construction, flooring, desks and chairs it was about £5k tops. A bargain to my mind and it’ll easily last 25+ years.
Sounds like it also doubles as a nice man cave (and woman cave / she-shed?) as well!
At the time after I got certified, I bit the bullet and bought my “travelling” scuba gear (BCD, regulator, computer) and that was a pretty big initial outlay (given my salary at the time). But not only has it been well worth it, but it also facilitated other big-ticket purchases: killer dive vacations.
Some years later when I decided to get into u/w photography, I started with a pretty mediocre point-and-shoot digital, but opted for a serious (and expensive) underwater strobe. I’ve gone through 3 cameras since, but the strobe has become a mainstay. And I finally have a photography rig to take decent pictures with (at least ones that I’m happy with).
This one is more practical than sexy, but it still makes me happy. About a dozen or more years ago, we bought a mulcher/vac to tow behind our mower - similar to this, but a different brand. At the time, it cost us $1100 and I really cringed, but has it ever been worth it!!! Just yesterday, I dragged it around the front and back yards and in an hour or so, I’d cleared most of the leaves and dumped them in the wooded part of our yard. In all those years, I don’t think we’ve spent over $500 on maintenance for it and it performs like a champ. I 
it greatly!!
As for boats, we’ve owned 5 sailboats (plus a Hobie cat, but that doesn’t count) and lived aboard 2 of them. Each in its own way was great, but about 11 years ago, we sold our last one. And next week, we’ll be owners of a 36’ Grand Banks trawler, and we’re very excited about it. Spousal unit want to do the Great Loop, so we’ll spend the next couple of years getting to know the boat and honing our skills, then with luck, we’ll drop the dock lines and head out. In the interim, we’ve got the whole Chesapeake Bay to explore!
Hobie Alter and I disagree! Hobies are fantastic boats, a great way to learn sailing. 