My own problem with 'insulated' butt connectors was that the layer of insulation makes it hard to feel and differentiate how much I was crimping the metal part of the butt connector underneath the insulation. That's, the stiffness of the insulation gave a false sense of the tightness of the crimp. Crimping at odd angles on the bike didn't make things easier either. Obviously, might just be with me.
Btw, agreed, it's better to leave well enough alone because you can always, always, retrace your own steps should things stop working down the road. This is even wiser if you've configured the wires, etc., different from the stock setup. Modifying a modification plays havoc on the memory. If the stock setup is in place, you have something to reference off. This is not so with a previously altered setup. People may scoff at this, but it's easy to get your 'lefts' mixed up with your 'rights' on the rear wiring. In one instance, you're facing the front of the bike, then the next instance, you're facing the back of the bike pulling wires, and if you've heaped on converting the rear single-filament to dual-filaments, then you may be so busy focusing on which wire is the high, and which wire belongs to the low, that you lose track of your lefts and rights dyslexic or not, until, like anything else, you eventually develop a better feel for it. I guess you could work on one side signals at a time, but it's more cumbersome.
On 'crimps,' I wish people (in general) would stop being so cavalier with the step on behalf of the less experienced crimpers. If you practice 10 crimps while you're in front of the tv, and tug on the crimps the next morning, about half the crimps will pull off. That's working on a flat surface. On the bike you're crimping at odd angles and vibrations tend to exacerbate defects that wouldn't even pose a problem on home electronic equipment. In that sense, crimping is a skill in itself. Nowadays I simply solder any joints and shrink wrap it. I even add a layer of sheathing over the shrink wrap tubing. No, plasitc sheathing and shrink tubing are not the same items. By the time I'm through, a 14 gauge wire ends up an inch in diameter. That's not including a layer of electrical tape if I'm up to it. If you plan later on running wires under the rear fender, I think the better thing to do is sheath the wires. There are pre-wired sheathing or you could fish wires through empty sheathing.