Originally Posted by R. Stratenstein
1. I have not wound very many pickups, but from my research on the subject, I leave the starting end loose, taped behind the bobbin to stay out of the way, until the coil is fully wound. So the first step is to leave a fairly long pigtail, and wind the first few wraps by hand, until the wire is secure on the bobbin, then I carefully fold the wire under the bobbin, and secure it with a piece of masking tape. When done, I check the resistance on the coil before and after soldering the coil wires, and the lead wires to the eyelets, to make sure I've got a good connection.
2. Hot/ground are determined, as noted above, by which end you solder to the ground, and which you solder to the lead that runs to the circuit. If done carefully, you could reverse the leads if you don't like the sound. Personally, I don't think that (or direction of wind, etc.) makes much of a difference, as long as you pay attention to the phasing, and some guys like out-of-phase pickups, so that's a variable, too.
3. Yes, I think you are crazy to consider winding completely by hand. At the least, you'll consume far more time than it's worth, for no benefit. A while back one of our more accomplished builders, Scatter Lee, wound pickup(s?) using an adapted fishing reel to turn the bobbin. I recall his comments were to the effect that he'd had enough, and was going to find some kind of electric machine to do the turning. Eight to ten thousand of anything, done by hand, is a hell of a lot, and when you're trying to maintain a consistent tension on the wire, and manipulate the wind pattern (be it the mystical "jumble-wound", or carefully laid parallel layers), I can't see anything in it for you but hand cramps. Buy pickups before you do that. Or at least adapt an old fishing reel.
4. I can almost guarantee that you'll produce pickups that sound as good as, or better than factory ones doing it yourself. For my first shot, I bought StewMac's kits for bridge and neck Tele pickups, 42 and 43 gauge wire, and tried to emulate as closely as I could, factory pickups. I was extremely pleased with the results, and saved a bit of money, too. The process does involve several steps, some specialized parts, but is not difficult, or require special skills.
By the way, for me, the biggest challenge was to develop the right "touch" to maintain tension on the wire without breaking it. Took a couple of false starts but I finally caught on. This is about the only way you could be "no good" at it, and I can't imagine you not learning at least as quickly as I did, how to hold tension just right.
I'd encourage you to give it a shot. (Using at least a mechanical aid, like a fishing reel, or an old sewing machine, etc.) You never know how well you can do until you try. I think some guys have tried successfully to wind their own pickups, but have decided it's better for them, to purchase ready-made pickups and spend their time working on other aspects of the instruments they build.
And you can probably always buy some bargain pickups cheaper than you can wind them yourself, maybe even find used botiques and factory pickups of high quality, also cheaper. Winding you own, you have the satisfaction of having done it yourself, and you know how many turns of what wire, going in what direction, with what magnetic pole goes in which direction, and all the other little details.