Ok
In reverse order:
1) You do not have to bore from that side. You can also bore from the other side, just compensate. Here is a really nice video from Sweden that was posted here on arborsite.com showing the start of the bore from that side of the tree:
Go to:
http://www.skogforsk.se/KunskapDirekt/default.aspx?p=11362&bmp=11727
then:
Film för bredband
then:
Avverkning med motorsåg (10 min) the bore is at about the 2:10 mark.
(other videos and info of interest are also there)
A huge reason for this is sooner or later you're gonna get a tree that the only way it can be cut on safely is to make all your cuts away from below the hazard. Which of course, may well be on the back-cut cutting side in this video.
2) The second reason is it gives you the cleaner safer escape that doesn't involve the crossing behind the tree/snag. I'm not saying that you needed a second escape path, or that you should have scaled walls and gone through the house, just that you can smooth out that first escape by finishing your cuts on the same side as the escape.
3) You can still lean into your saw to give it some oomph with a good grip. Please be aware that your forcing the saw in is not what prevents kickback.
"the fact that i only weigh 130 lbs i have to lean in with a little more force than other guys do to make this cut to prevent kickback." It is the tip angle/finesse of the entry that prevents kickback. What a good grip can do is help control a kickback range of motion, to a degree. Putting more force into the cut, should the bore have been miss-started, will result in a greater kickback. Not a reduced one.
As for your being comfortable with whatever style. No problem. Just that when you post a video of using sights inaccurately, expect a comment or two.
And: Go with two pulleys for some mechanical advantage, (wind or other issues), and three for mechanical advantage plus relocating the puller from under the trees intended lay.
I like my rakers at 30 thousandths because we cut mostly dead wood, would go with 35 over the 25 thousandths that most chains come with. But solid dead is so prone to kickback that I don't go lower.
But: My Father-in Law would take a 10-12" flat mill bastard to every new chain and do 5 strokes on the depth guides. Major pile of metal filings at the bottom of that vise. I'm not man enough for that myself.