You should run the mash tun dry for each runoff. Otherwise you're intentionally leaving sugars behind.
Yep. What you want to do is measure how much runoff you get from the mash. Subtract that from the amount you want to boil. The answer you get is how much sparge water to use so that you have nothing left behind.
I guess I stumbled upon the approximate correct technique by accident. This is what I've been doing, basically. Wind up with about 6-6.5 gallon pre-boil, about 5 or slightly less after (depends on how much hops, mostly).
Drain mash tun till it's a slow trickle, then add sparge water, then drain again, then add sparge water, then drain final time. OG works with beersmith II if I use 67% efficiency (top of design page input).
Beers have been coming out fine since I made adjustments and figured it out. Even before then, they were good but my OG was low. Adjusting efficiency on beersmith was key (for me at least).