A few years ago I found (and bought) a Mec shotgun reloading press in 28 gauge for $15. It works great and I still use it. Those kind of quality tools never wear out. Haven't seen any deals recently.
Young neighbor showed up with 4 or so sets of mostly rifle dies in good shape that were for cartridges I reload, bullets and brass for 38 special, powder for it. He'd paid $10 for it in a garage sale. In exchange for it, I made a simple repair to a broken stock on his 30-30 and gave him $10.
I picked up a Ruger 10-22 for $75. It had been reassembled wrong. Took it apart and reassembled correctly and it was fine. I picked up about $400 worth of reloading stuff for $40. I have not been going to garage sales lately. Been too busy.
My friend called me at work one day to tell me he had seen some reloading stuff that he didnt want. He said the box had lots of stuff in it. I said if he could get it for $30 I would buy it. He paid $40. I was bummed until I saw it. For $40 bucks I got an RCBS lub-a-matic II, over a dozen dies for it, and about 30 top punches. There were also 2 RCBS bullet molds with handles. And a 44 mag hollow point devistator mold. There was so much 44 mag reloading stuff in the box that I decided to go buy a S&W 629 so I could shoot it.
I never find garage sale deals, so I quit stopping, always old books and baby clothes and crap like that, or old junk fishing rods. I went to tons of sales when I was a kid with my parents and grandparents, never saw any good gun deals even then though I live in a rural, small town atmosphere where those sorts of deals are gone right away or stuff is sold to a friend or whatever before the sale starts most the time. Probably easier in bigger areas to find that stuff.