Ok so I’m all done after 30 minutes, and the headphones work and sound better than before, so here are some tips (BTW it seems to be a common thread that the tip of Grado headphone jacks are falling off).
1.) I already had the solder gun, wire cutters, and a voltage meter. So I bought this 1/8 inch gold plated headphone jack at Radioshack for $5.
2.) Watch this Youtube tutorial for a step-by-step of how to replace a jack. It’s incredibly easy.
Update: since this Radioshack jack came with screws, I recommend soldering the actual wire so it becomes hard and then lightly screwing that to the jack. This is better than soldering it to the metal jack because if you have to change the wires in the future it’s as simple as unscrewing something rather than the mess of unsoldering something.
3.) Sending it in for repair at Grados headquarters didn’t make sense because it would have cost half as much as the headphones original cost, nor did it make sense to buy a new pair of headphones because I loved my current ones. Aside from the tip falling off, the audio was cutting out at times from the solder coming loose underneath (so I frequently had to bend the jack, which is probably why the tip eventually came off).
4.) The “spring” at the end of the Radioshack jack wasn’t thick enough to slide over the Grado cable, so just throw that out. I used electrical tape to replace it so the new cables weren’t exposed. The springs purpose is also so the cable doesn’t become frayed over time. So I’ll just plug/pull my headphones from the jack for now on.
5.) The Grado SR60 has a 3-conductor tip-ring-sleeve (TRS) setup. However, there are actually 4 wires when you cut into the cable. The 4 wires are red, right, and 2 blues - see picture. For the blue wires, I just rolled them together as one. I believe the higher Grados are a 4-conductor TRS, but don’t quote me on that.
6.) I’m assuming it’s standard, but my original Grado cables were incredibly long and always in the way (probably 6 feet long). So this was a good opportunity to cut off about 2 feet of excess cable, which is something I’ve wanted to do for years.
7.) After soldering and everything was complete, I noticed one of the headphone’s ears weren’t working. I discovered it was from the jack’s wires rubbing against each other after I slid the new cover on. To resolve this, I put electrical tape around the wires - see below picture.