I got a car seat and a high chair for $25, still use both of them.
I got a handheld jackhammer thingy for $5 which Mr. Mouse loves.
I got a set of three nesting pyrex bowls, opera glasses and an old huge atlas for free, all because my kids behaved while we were there!
got a really nice Tripod for my Camera, think that was $20
and an Automatic Breadmaker $20
Both of with where priced in the 100’s new
so I am pretty happy 
I don’t usually shop at yard sales because I have too much crap already, but we stopped one time for giggles. Turns out the woman had just divorced and was moving back home, so she had tons of Corning cookware going for cheap. I got a bunch of it for $1 and $2 a piece, and I’m still using it today.
a sad clown painting on black velvet.
My friend and I saw it at the exact same time. It is/was the only fight we ever had. I kept it for a few years and then gave it to him as a wedding gift.
For some reason I don’t think his wife likes me very much.
Most of my stuff has come from garage sales or bought from freinds/family. The best deal was probably my little brother’s clarinet. We had no idea if it was in good shape or not, and they were asking $35. It took $125 to repad and the music store guy said that model cost $1k new.
Funny story Jorel, nice of you even if it was a velvet clown painting. 
I mostly buy hardback books, but every once in a while I find some great deals on other things. Probably the best was a steamer trunk I paid $5 for. As we were loading it into the back of the truck, someone offered us $200 cash for it. I have no idea what it’s worth, because I wouldn’t consider selling it. I’ve seen ones similar to mine in antique stores in the $400 - $500 range, but I’m sure that’s with a huge mark-up.
I found a 78 of Rosemary Clooney singing “Mambo Italiano.” $1.00. It was in a volume of 78s that were from the same era. I still have it.
Oh my god. Jorel just reminded me.
Once I found this godawful cribbage board. It was a bowling pin that had been sawed in half, then encased in acrylic (the holes were drilled in the acrylic). It was horrible.
But–we had a friend who was getting married, a friend who LOVED to bowl AND play cribbage. So it was a wedding gift. I was so proud.
I got a piano for $25. the woman selling it was moving in 2 days and was desparate to get rid of it.
When my brother and I were young, we were hooked on He-Man and She-Ra. We positively lusted after a playset called “castle grayskull” or something. It was this green castle in the shape of a skull that folded open like a dollhouse. We had all the figurines, but not the castle. My parents didn’t want to buy it new, b/c it was expensive, but they would get us to come along to yardsales with the excuse “hey, they might have a castle grayskull!”
One day we actually found this castle grayskull, and my parents were horrified that it was being sold for $50. Of course, they couldn’t really tell us that we couldn’t have it, b/c the possibility of finding it was what they used to drag us to these yardsales in the first place! So they tried to talk the man down a bit, but he was quite firm in the price. After about 10 minutes of trying to haggle, the man’s wife comes out. “Oh really, hun!” She says in disgust. “If they want that dusty plastic shell, give it to them for $10. I can’t believe you think anyone’s going to pay more than that.” He gave his wife a look and took our money. I remember my parents booking it out of there as fast as possible with the castle!
We still have it in the basement