So lots of years investments:
FInishing the basement and putting up a big screen and a projector down there made that a safe space for my kids and their friends to hang out clear through college so knowing where they were and that they were safe was worth every dime and I'd do it again in a heartbeat for even twice the amount.
The family vacations and taking the kids out of school were worth every dime and sideways glance I got from the other PTA & Sports moms. I sort of wish there was a PTA reunion so I could blast, your kids ARE NOT doing better than mine and vacations didn't ruin them, in fact my kids say they had the perfect childhood... I want a sports mom reunion too

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Dumpster, I wish I did one every 5 years or so, it is awesome.
Moving bed, got it as an indulgence but it saved me as I recovered from surgery.
TIVO, back in the day it was the best tech we ever adopted.
ADT, having my house alarmed ages ago gave so much peace of mind, not sure I would do ADT but having an alarm is really very calming in some areas.
Flowers, getting fresh flowers is such a mood boost, they don't need to be expensive.
Steam cleaner when my kids were little, no words for how great it was.
Awards & Bonus for good grades, I would like to toss this one up at the PTA & Sports mom reunion too.... pffft.