I spent for memories — in early 2019 my wife and I took our 3 adult kids and my 80-yo mom to Alaska to see the Iditarod dog sled race. We saw the start in Anchorage and then the finish in Nome. In between we did some sightseeing on the Kenai peninsula, including going to a musk ox farm.
Our own @Chefguy gave me some great tips because as many of us know, he used to live there.
We have many great memories from that trip.
We’ve gone more for the experiences, than the “stuff” (though we have plenty of clutter around the house that would seem to bely that).
I’d have to say either our current house (though as we age, the maintenance etc. is something we look forward to getting away from), or the car we bought last year.
The house: we were in a not-too-large townhouse, and the market had just started going insane in 2002, and we decided to take the plunge. Extra bedroom! Larger rooms!! 2-car garage vs parking spaces!
The car: We’d been getting by with a 22 year old Civic, and a 15 year old CRV. When the Civic said “I’d like a mortgage payment’s worth of repairs, kthx?” we said “no, no you don’t”, donated it, and bought a new CRV. White like the other two (we tend to buy at the end of the model year and that’s what they have available) - but we splurged bigtime and went for the top trim line. Some features we don’t use (integrated wireless charger that doesn’t work on any of our phones), some I thought I didn’t care about (heated seats??? hands-free lift gate??), some that we really, really wanted (seats with memory so we could adjust with a touch of a button, parking assist technology). It’s a genuine pleasure to drive and if all goes well, we’ll have it for 10-15 years.
On a smaller scale, I’m currently wearing a pair of Bose QuietComfort headphones. So comfortable I can wear them for hours without any irritation. I can listen to an audiobook on the subway or an airplane because the noise cancellation is so good (too good sometimes; household members have come up behind me and scared the crap out of me).
My biggest expenditure was $44,000 on a house, 43 years ago. We’ve made many improvements since then and looking back, I realize it was my most satisfying purchase as we continue to be the beneficiary of that decision.
My 2021 Mazda CX5.
I dragged my feed for more than two years before purchasing - my 2007 Jeep was still running like a top and perfect for me.
Driving the Jeep to the dealer to turn it in felt like I was bringing a pet in to the vet to be put down.
But I got over it. 
mmm
Our roof!
When I moved in with my gf she was in the process of getting a new roof for the house. I had just sold my house and had plenty of money in the bank, so I suggested I pay for the roof.
The house had a nice porch on one end that was rarely used since the roof didn’t cover it. The porch was not used if there was rain or intense sun.
I talked to a contractor about replacing the old roof but also extending the existing roof to cover the porch. That porch went on to become our most used outdoor space.
For a very long time, I outright rejected electric gardening equipment (either too underpowered, or needs a cord, or both).
Recently, after a test-drive, I took the plunge and got a battery-powered push-mower, leaf blower, and chainsaw (Ego brand).
Now when I want to do lawn care, I just push a button and go. No more wrenching my arm on a pull-crank. No more buying ethanol-free fuel to keep the engine from gumming up. No more mixing fuel oil. No more spraying starter fluid, no more soaking a gummy carburetor. No more 100dB noise, dirty exhaust, fuel spillage, oil refilling, knocking dust out of the air filter, changing spark plugs, tuning the carb mix, replacing the pull rope. No more unsafe, smelly gas cans sitting around in the basement.
The only complaint I have is that the chainsaw is slightly underpowered, so I feel like I need to sharpen the blade pretty much every time I use it. Also on the leafblower, I’d try to find a backpack model next time. Although the form factor is as small as most hand-carried blowers, the weight of the battery affects the ergonomics.
So yeah, battery lawn equipment is now having its moment. Highly recommend.
I love our battery operated chainsaws (a small one my gf can handle and a full sized 16 inch bar). I mentioned to a friend about having to sharpen the chain with almost every use and he told me that’s how you’re supposed to use a chainsaw.
After one of the burners on the stove died, and a neighbor’s fridge died, meaning they had to replace the fridge*, we decided to renovate the kitchen. That was 9 years ago and I’m still really happy with the kitchen.
This spring, we got our patio glassed-in, so now we have a 3 season room. This summer was the wettest in 3 decades, so we were really happy we did that this year.
Many years ago, I was a STEM student before it was called STEM, and before students were expected to have personal computers. Students purchased calculators from Texas Instruments, Casio, and Hewlett-Packard, with Hewlett-Packard being the priciest of the three. For someone on a student budget, and allowing for inflation, this was certainly a “big-ticket” purchase.
I purchased an HP-29C and never regretted it. It was as though someone peered over the shoulder of STEM students as they did their homework, and designed the calculator from that. And the overall shape was perfect for holding in the palm of one hand while the thumb moved back and forth clicking the keys.
Later I was to purchase newer models of Hewlett-Packard calculators, and my cell phone and laptop now have emulators for them - but nothing has brought back the satisfaction of that purchase.
My metal lathe.
I just went the other direction - trading my GTI for a freaking Suzuki dishwaher/Forester. 
No chainsaw, but got the mower and trimmer/blower. Not a luxury, as the old gas mower crapped out. If not a pleasure, it sure makes lawn care less onerous. Truly the best tech for anyone w/ city/burb-sized property.
When I was at school from 1984-8, the HP 15c calculator was the one to have. $300 at the time, which an inflation calculator tells me is about $800 now.
This is almost the same for me, but I went with a Saris. It is just a bit more work (takes me 30 seconds to load a bike and secure), but it works for all our bikes: Road, mountain, and e-bike with fenders (the fenders makes it tough for most bike racks of this style). This rack is so much better than our previous model and it allows us to get into the back of our Subaru with bikes on the rack (dog in and out). I still have roof racks for our light road bikes and sometimes use it, but it’s mainly the Saris now.
Eh, maybe so, but I could get at least 5x more cutting time out of the gas model without needing to sharpen it.
Still, I’m fine with the tradeoff. With the battery-powered, I know I just have to charge the battery and sharpen the blade. With the gas model, I always dreaded finding out what exactly I’d need to to do crank it on any given day. Might be just fueling, might be some starter spray, might be pulling the crank for 20 minutes, might be something else.
Good riddance to gas. Can’t wait to get a fully electric car.
The general rule for when a (gas) chainsaw blade needs sharpening that I go by (can’t always judge by degree of difficulty because different types of wood are more difficult than others): if the blade is creating wood chips when you cut it’s plenty sharp. If it’s creating sawdust it needs sharpening.
I probably have no business owning a chainsaw. I have no idea how to sharpen one, and I’ve used mine on and off for about 5 years now.
And if there’s smoke, you’ve waited too long.
I keep three or four chains at home. A friend sharpens them for me from time to time. I just put a sharp chain on when I start a project.
I used to take my blades to a shop to have them sharpened.
Then I worked at a place where I could buy chainsaw blades at a 30% off employee discount, which made them almost the same price as a sharpening.
Then I bought an electric chainsaw sharpener from Harbor Freight, which would have paid for itself in a few sharpenings, but it was a cheap piece of crap that fell apart after a couple uses.
Next time I might just try my hand at doing it by hand. It’s not too difficult, it’s just tedious and requires the right type and size of file:
…and if it is supposed to be freshly sharpened but does not cut at all, check to make sure you put it on the right way (yes, this happened to me. Fortunately I figured it out before I irately called my chain sharpener guy 
)
The $215 I spent on lumber, as well as the vermiculite, peat, and compost soil medium necessary to construct and fill my raised garden beds over 15 years ago has provided many hundreds of hours of enjoyment.