Why bore? I avoid boring whenever possible. Is there a good reason to bore vs. just a 2" deep cut in the top and then back blade from the bottom and pull the saw as log starts to fall ?
From the looks of the rocks in the creek bed and visualizing flood season, OP's boss's 'chi' would be better served by letting it be for a season or 2, looks like high water will move it by next year? Is not the 72 yo yuppie definition of chi something like 'natural effects' or ' Ghia will take care of it' ?
My approach and reasoning is not based on this case this small task before us.
It's with a hard day's work in mind and perhaps 24 consecutive days begining or comming to end. It's always about fatigue. Doing the most work expelling the least amount of energy.Its about controlling your environment. "Plan the work & work the plan" If this was my easiest job of the day then I would try do it at the end of the day. Obviously that's a perfect world & not always realistic. I have the great big picture approach. I never give advice like Its their only job they will evey do. If that was the case, I wouldn't bother. I'd probably spend my time talking them out of it.
Practice and comfortability of a different technique:
Works great for removal of a lot of leaners (fire ladders) in a days cutting.
It's very strenuous to underbuck at heights all day. (*Do not try it with the possibility of side bind)
With very low clearance it's also the way to go. People try cut what they can from the top but they end up lowering the log on every attempt. Apart from what
@Ted Jenkins was describing. Ted is creative, you can tell the experience level there.
His technique with the wedges should be a consideration and practiced. Whether one carries wedges or not. It's all tools for the "bag' right?
I agree that with this log, most experienced guys would probably cut 2-4 ft lengths cutting from the top about 40% then underbuck them off. Then block them from the top and muscle the lengths to roll and finish blocking.