Oh man, I'm the king of cheap gear, especially cheap used gear. I scour the interwebs all the time for good deals/good excuses to buy stuff.
1984 Ibanez DT250 destroyer. My first guitar, bought it for $199 back in 1994. Still have it today, and it's the best sounding guitar (for metal) I've ever played. I finally just picked up a case for it and put it away, and built my own version of it so I can let it rest and age gracefully, since I've beat on it over the years.
Ampeg SS140C - $120. Excellent sounding solid state amp, even the distortion! It was a combo that someone tried to turn into a head by bolting the amp itself to a scrap piece of particle board. It looked horrible, and worked perfectly. I bought it and built a new enclosure for it. Very happy with it.
1960s AlNiCo speakers - you can get these on eBay all the time in the vintage electronics section for $20-$30. I play the above mentioned ampeg through a 15" AlNiCo speaker from 1964 and it sounds fantastic, albeit a bit of a one-trick pony. They have a low power handling though, so you have to be careful
Peavey VTM-60 - basically a Peavey clone of a hotrodded JCM800. I bought the head as just the chassis with no enclosure and new JJ tubes, for about $150. No complaints here, it sounds incredible and I'd recommend this amp to anyone.
Rogue LX205B - $150 for a 5 string bass. I picked mine up about 5 years ago or so and I still use it all the time. It's nothing special but it sounds good and gets the job done and at least on mine, the fretwork and overall finishing are great.
Bugera 6262 head - $250 used. Some people have negative opinions of Bugera amps because a lot of them are basically copies of more expensive amps, and their early ones had some quality control issues. I love them. It was my first tube amp and sounded absolutely incredible. The only negative for me was that it was a 120 watt tube half stack and I'm just a home studio musician - this thing puts out deafening volumes. But they all sound good! I'd love to pick up one of their 333XLs.
And most of all:
Reaper! $40 or something. Can't remember, I bought it in 2009. Before Reaper I was using a shitty digital 8 track and making shitty music. Once I switched over to Reaper I started learning a ton and my music improved exponentially.