Not bad at all! Few tips for ya...
...the trick to guiding the wire is to relax your hand. Keep a nice firm pinch on the outer wire but keep your wrist, forearm, and elbow loose. You just kinda have to feel it out. Start off at a moderate speed and very carefully adjust the angle of your grip until the wire falls into a groove. From then on, do not move your hand intentionally and try not to lock-up, the wire will not only begin to wrap itself, but advance your hand for you. Your index finger and thumb are just there to keep the outer wire pressed up against the core. Don't pinch it too hard - just keep your fingers right there. Once it locks into place, you can crank the drill to max speed and it'll stay right where it needs to be.
The only way to really get it down is to practice. A few sessions of claptoning as much wire as you can before your drill dies should be all it takes for some major improvement.
And as far as the outer wire sliding off of the core and stretching out while wrapping coils goes... ...the trick I find tends to work the best is to fold maybe an 1/8th of an inch of the end over itself and pinch it tight with pliers BEFORE removing the finished wire from the chuck. Do the same for the other end and carefully clip the excess that was jammed in the drill. If you do it right, that outer wire has nowhere to go either way, so you don't have to worry about continually having to push it back or avoid tugging it loose while you coil.
Also, another thing that makes the outer wire easier to work with is to pull a couple of feet off of the roll, lock the wire back onto the roll, tie it around a door-handle, gently pull the wire taught, and walk the spool back about 20 feet. Slowly pull it tight a few times before walking the roll back to where you're wrapping the wire. It becomes a lot easier to work with when you pull all that you need off of the roll first and straighten it out than it is feeding it fresh off of the roll. 20 feet should be enough to do a foot and a half of clapton...
...which reminds me, you'll have an easier time doing enough for one coil at a time. 6-8 inches of wire should be more than enough core wire for one and will be more stable at high speeds. And really, once you get the speed up, it only takes a few minutes to twist-up enough for several coils.