sudomod

So I watched many videos on soldering technique before I started this project. The technique was always to get the wire and board in position with helping hands or tape, then hold the iron in one hand, the solder in the other and feed solder into the heated joint until the proper amount is there. None of the videos I watch, wermy's included, do this. Everyone holds the wire with one hand and the iron with the other and just dabs the connection. Is it just not important to do it "correctly"?

If most people are getting some melted solder on the iron and then applying it, they don't get the benefit of flux, right? They also are at risk of a cold solder or whatever. It looks WAY easier to do it this way than the way I've been doing it.

What am I missing here?

You miss nothing... lol.
For wires, i pre tin them, pre tin the pad, and then melt the pad will diving the wire on the melted solder. Never had a problem...
I am doing your described technique for my electric rc car which uses 10AWG cable, they are more difficult to solder

"Proper soldering technique" will yield better results and have less risk of damaging the pads, but there are several ways to cheat it.

Both when i was taking classes and when i soldered my own stuff i just got annoyed at that technique. Always tin the wire (even solid wires) and it makes it much much easier to attach wires.
Through-holes i personally find it easier to pre-solder the pad, then heat it up while i poke the wire through and cut excess off afterwords.
Pads are same thing though im not pushing them through obviously.

I may have terrible wire management in my first GBZ but im not worried about my "cheater" soldering job at all. In fact i work at a radio company and none of us use the "proper" technique when soldering lol.