Electric chainsaw sharpener

Nope your not crazy ,the rest of the world is
Welcome to FHC Mathewsmatt

 

I also use a dremel to sharpen my chains.
I use diamond coated bits I get on ebay.
They last longer than the stone bits.
When a bit does get a little worn I save it to use on the rakers.

 

When I say "Dremel type tool" I don't actually use the brand name Dremel, but use a similar type rotary grinding tool specifically designed for sharpening chainsaw teeth like this one.

It has an angle guide to get the right angle, even so it takes a bit of practice to hold the right angle and take just the right amount off. Of course using a hand file also takes practice to get the right angle and stroke, the advantage of the rotary grinding tool is it's much, much faster, which makes it a lot easier to grind off more then you really need to. To tell you the truth, taking too much off was a mistake I was making for the first chain or two because I got a little carried away playing with my new tool and it was so much easier then hand filing. I have since got a lot better at using it, and consequently my chains last for years and years now.

To file down the rakers I use a standard raker guide like the one below but just use the grinding tool to grind them down instead of a flat file,,, again it's way quicker, but because you have that raker level guide there to limit how much you take off there isn't the worry of taking too much off.

 

I wouldn't say you are over thinking, just thinking it through, which is a good thing.
On that point,,, One thing I also do is reverse the polarity of the leads on the rotary grinder when sharpening the teeth on the opposite side of the chain and hold the grinder facing the opposite way, that way the grinding wheel cuts the teeth the same way for both sides. I never have a problem taking more off on one side or the other.