$5,000 down payment. I bought a condo when I was 25 instead of renting. The money I made off of the condo allowed DH and I to buy a single family home when we got married last fall.
$2000 (I think?) option package on my Saturn. A/C, power doors/windows, keyless remote, etc. I decided that if I was going to be driving the thing for the next 10 years, I should at least have all the options I want. That was 8 years ago and I've never regreted it. I'll do the same on future cars!
$100 for my feather bed. It's so soft and WARM!!!!

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$300 for my dishwasher (the "new" house didn't have one at all). 'Nuff said.
$400 for the Richard Petty Driving Experiance for DH (then my fiance). I've never seen him so happy! The rest of the trip, he'd randomly look at me and say "I drove a race car!" When I showed his mom the pictures, even she remarked that it was the biggest grin she'd ever seen on him.
$0. Adopting my dog Missy from someone that couldn't keep her anymore (due to circumstances beyond her control, she hated to give her up). The best things in life are free!