What have you spent money on that you felt was worth the expense?
Great thought-provoking question, Al!
The Aloha Stadium Swap Meet vendors have these deals on five t-shirts for $20...
But seriously:
1. I've upgraded my "one-time expense" threshold from ~$10 to ~$100. If I'm intrigued by the potential value of a one-time expense but find my sphincters reflexively clenching at the thought of spending that much money, I stop and think it through. I used to automatically decide not to spend because it was "too much". These days, over half of the time I decide to try it and it's almost always worth it. Examples include an online continuing-education course, buying books on Amazon.com after I've been stalking them at the library for a couple years, and taking a Waikiki staycation for a conference to avoid three consecutive days of town rush-hour drives. This "one-time expense" only happens a few times a year, and we still try to avoid recurring expenses which still have no value to us-- like HDTV digital cable bills.
2. Technology that's become a lot more affordable. Several posters talked me into finally buying a wireless router. (Immediate & immense improvement in family quality of life.) TiVo. Kid's cell phone (her money). I helped our kid with her iPod Touch spending decision (her money) and it's been a valuable process leading to a Macbook and an iPhone (college fund money). A new desktop with a "free" 23" monitor. I'm inching perilously closer to buying my first iPod (waiting for the right Craigslist deal).
3. Capital expenses with reasonable paybacks, especially considering inflation. This includes a photovoltaic array, a solar water heater, a water conditioner, EnergyStar appliances, and radiant foil attic insulation. Low-maintenance landscaping. It even includes a lifetime TiVo subscription instead of a monthly/annual plan. The next step is more xeriscaping and an indoor remote-monitoring water meter (to keep a closer eye on leaks).
4. A 2006 Toyota Prius, bought used in 2008 through Craigslist.
5. A literal houseful of upgraded furniture, purchased one piece at a time over several years through Craigslist for at least a 50% discount over retail (and usually 70-80%). Maybe we feel this way because the furniture we bought in our 20s was pretty much destroyed by Navy moves.
6. Big hairy complicated home-improvement projects. If you're going to live in a place for more than five years, it's probably worth figuring out exactly what needs fixing and then seeking professional help. In our case we took almost a decade of discussion/planning to finally repair our backyard lava-rock steps, replace a decrepit concrete lanai, and upgrade our lanai/sidewalks from crappy crumbling FuturaStone to stamped concrete. (A general contractor and two subs.) It's cooler, we love sitting outside on the lanai again, and it's easily returned over 100% to our home value. Next up is a custom pergola to shade the south side of the house, perhaps roofed with more photovoltaic panels to supply recharging power for an electric vehicle. And when our pet bunny goes to his great reward in a few years, we're going to completely renovate the family room that he's been chewing on.
7. Quality power tools. A lot easier to find and a lot less expensive than they used to be. We may rent them if it's not too much of a hassle, but it's even worth buying them for a one-time use and then reselling them over Craigslist. Even 20 years later we appreciate improvements like laser sights, LED task lighting, and better stud finders.
8. Taekwondo. Wish I'd discovered that years ago.
9. Flying in "more legroom" class, business class, and even first class. Well worth it for those 8-10 hour cross-country/international flights. I also try to avoid flying redeye if there's a realistic alternative. It's just not worth the hassle of putting up with airport delays, talkative pilots, screaming babies... all while trying to catch up on sleep and arriving before the hotel room is available for checkin. This only happens once a year or so when I travel on my own. Spouse claims to not be bothered by submarine-[-]density[/-]quality seating but I've had enough of it.
10. Surf school. I'd reached a plateau in my skills and I was hesitant to seek out North Shore spots. Two pros spent 15 hours (over five days) showing my kid and me the breaks, the techniques, and surfboard-design issues. Huge improvement. After the school our kid really got into designing her custom board (an early graduation present) and enjoys surfing more than ever. As a side effect, I now have more places to surf than I can realistically handle... but I'm going to keep trying!
One lifestyle change that we haven't quite figured out yet is "recreational travel". We're great at "travel with a purpose"-- accompanying spouse when she was on Reserve orders, attending family events, or traveling to conferences. But we're still not very good at "what the heck, let's take a cruise next week" travel. We'll work on this in another 136 days when our kid starts college...