My very first electric rig was an old 60's Silvertone el cheapo and some Peavey amp with an 8" speaker. It sounded gawd awefull, but mainly because I didn't know how to play anything. I sold the amp, but kept the guitar since my grandad gave it to my dad and his brother (which they never learned to play) and then gave it to me. Then I started playing an old acoustic that used to be my mothers. The bridge was bowed up, and the neck was coming apart from the body. So, let's just say that it didn't have very low action. It was so hard to play that it almost made me give up. Thankfully my mother wouldn't let me.

Other than that, my worste gear experience was with a Peavey Classic 50/50 power amp I bought off of ebay. Fist, it took forever to get the darn thing, then, after I did get it, it only worked for about 2 hours before it died. Never could get it fixed, so I ended up selling it.