Not sure about the electric gloves, If they don't pull alot of juice, you might be able to do it
It's pretty reliable with regular maintenance. You'll have to deal with certain known issues, maybe, or maybe not. Depends on how lucky you are.
If you are thinking this is going to be like an SV650, it's not. Alot slower too.
Vibration is more than anything with a balance shaft. Not terrible, but more than any Jap bike.
If you don't run it too rich, you won't have to de-coke the head until you need a valve job, which should be a while.
There are issues with things breaking off, and falling off from vibration, sometimes.
Starters break the sprags often enough to mention it.
It's carbureted, so you have to deal with jetting issues for weather conditions.
It's air-cooled, so you have to warm it up before riding.
If you are serious about not doing over 60-65mph most of the time, can tolerate 1000 miles of low-speed break-in time, and can deal with some of the quirks, then you should be able to be at home with the bike.
Regarding rebuilds, there aren't going to be any rebuilds with the Electra.
They don't supply spares for the engine crankshaft assembly. You have to buy a new short block, if you need a rebuild with the Electra. But, the bottom ends seem to hold up pretty good with the Electra, so you won't be likely to be needing a bottom end. I haven't heard any reports of any Electra bottom ends going bad so far. But some might have, which I haven't heard about. They have a roller bottom end with steel rod and decent oil pumps.
One thing is that it's not going to replicate Japanese bike reliability. I may not be able to predict exactly what things will happen, but they will happen. No Royal Enfield so far has been able to match the "appliance-like" ability to just "push the starter button and ride anytime/anywhere" without something happening sometimes. They are quirky in ways. Maybe not quite as quirky as the older Bullet, but not too far from it.
It's just not a Jap bike.
But the Bullets have a way of "endearing themselves" to you with their enjoyability and charm, so we tolerate the quirks and issues to get what we like.
I have an older Bullet which I really love, and it has always done what I've asked of it, with very little need of anything except some oil changes and cables. However, I don't commute with it. It's just my fun bike. It has never let me down.