askchapo

Depending on your location and infrastructure, a decent bicycle (and safety gear!).

Free transport, good exercise, very little that can go wrong with it that you can't fix yourself.

I am, however, painfully aware that this isn't necessarily safe or viable in a lot of locations.

Speed

There are several categories, and I'll keep below $500 in each category. I marked stuff with a ^ that has been life-changing for me personally, although a lot of these things I've always had and couldn't imagine living without.

Kitchen stuff: Skillet, small saucepan, larger pan, big cutting board, chef's knife, baking pans (loaf, cake, large sheet), measuring spoons/cups, decent spatula or two, plus $20 in dishes and silverware from a thrift store. Use whatever durable lidded containers as fridge storage, and empty glass jars as cups (or also as storage). Pressure cooker, (more versatile than a crockpot) food processor (more versatile and reliable than a blender), and electric tea kettle^. Appliances might be pushing it close to 500, and there are more gadgets that you might want, depending on what you prefer making, but these are the basics to be able to cook most things yourself. Cooking instead of relying on pre-made food saves you hundreds of dollars a month, and opens up so much.

Transportation: A bicycle^ that fits you well, and if you have the space for it, a bike cart. Hybrid bikes are great but expensive, larger mountain bikes are suitable and versatile, road bikes are good if everywhere you want to go is 5+ miles away. If you can cycle places within an 8-mile radius (or 12 if road bike) on most days instead of driving, you'll save a lot of money, and it's effectively half a gym membership- the other effective half is a yoga mat and maybe a pair of free weights. For everything that's outside the range of cycling, a bus/metro pass.

Tools: A drill, circular saw, screwdriver set, allen wrench set, claw hammer, adjustable wrench, needle-nose pliers, multitool, whetstone, plenty of duct tape and WD-40.

Furnishings: A decent mattress, box springs, and bed frame that's high enough to put storage totes underneath, plus those storage totes. An adjustable desk chair, and a spacious desk^ that you're neither straining at nor crunched over. A large table that can fit a lot of people around it, or a sizable project on top of it. Windowsill plants, for either air quality or herbs. A foldable stool. The more familiar you are with the tools, the more of this you can make yourself.

Terminal: A computer case that will fit all the hardware you'll ever need, and that you can run Linux on. A good-sized screen, keyboard and mouse and webcam, and a printer/scanner.

Clothing: A really good winter coat (with plenty of pockets), a decent rainproof windbreaker, a wicking layer/long johns^, a pair of rain pants, a good pair of work boots. At least 2 sets of dress clothes or semi-formal wear, because having a good-looking outfit gives you a real self-esteem boost. At least one set of really sturdy clothes that you don't mind getting dirty and worn. If you learn to sew and get yourself a sewing machine, you can make a lot of custom clothing, which is especially important if it's hard to find the right fit. Plus you save a lot of money and get a concrete kind of ownership that money can't buy.

Gear: A tent^ - unless you can never see yourself or any guests camping. A hand cart/dolly^ because there will be things too bulky or heavy to carry or move. A portable first aid kit, and a larger one for your home. A wireless speaker^. If you're musically inclined, your own instrument, plus a music stand and amp and even bigger speakers. A couple lamps^ for lower levels of light at night, or candles if that's your thing.

Miscellaneous (depending on your location and lifestyle, either absolutely essential or useless): A dehydrator, if you do food or seed or specimen preservation. A weighted blanket, if it makes a big enough difference. A water filter/purifier if you don't trust the water district or your pipes. If you have long and/or thick hair, a hair dryer. If you're in a humid climate, a dehumidifier^ (food spoils slower, clothes won't get mildew, deters some pests).

A good multitool to carry around in your pocket, I recommend Leatherman. The Wave+ I have is a nice tool, can also recommend the skeletool for something that's a bit easier to fit in your average pocket. Don't buy the cheap multi tools as they're generally rubbish to use and will not be a good experience.

If you don't have pockets that can fit a multitool, spend the remaining money on clothing that does have decent pockets and gain another real quality of life improvement.

I wanted to say a Playstation 5 but then I remembered it has no games to play

Glasses

If you live in a place with leaded paint painting over it or wallpapering over it will help your health to some degree. As a spoiler those waterproof peel and stick drawer liners from Dollar Tree make a reasonable wallpaper. If you rent beware of the stick, some of the peel and stick can really get stuck on if you leave it for a bit even though its supposedly a safe temp deal. For more decor improvements blinds/blackout curtains make a difference, especially if you have peeping tom neighbors or work on shifts. A lot of blackout curtains are nice to have in summer, they really do make the room feel cooler.

Good sheets/pillows and maybe a mattress topper, again more of a sales watch deal. Using a mattress topper I was able to get more life out of my 15yo mattress.

Tools are always good to have on hand.

My list could be some mix and match, or you could spend $500 on each.

Shoes/boots

Proper bedding/a good pillow

Percussive massage gun

A good office chair or your most frequent seating

Ergonomic keyboard and mouse

Pressure cooker

A cordless vacuum

Air fryer

A good dog or cat