There isn't anything to be gained by drilling the rafters, and some structure to lose.
Even high density rock wool batts are only R25 @ 6-1/4" (1' clearance with 2x8 framing), and if you're really have 1-3/4" clearance that's only 5-1/2" of batt thickness. R23 rock wool is the highest performance batt solution that fits. HD fiberglass would come in at R21, barely more than half the stated R38.
If the membrane roof isn't installed yet, putting a few inches of rigid foam between the membrane & roof deck would eliminate moisture issues in the thin section, eliminating the need for venting the attic and allows you to put the batts in contact with the roof deck. Per IRC 2012 chapter 8 you would need a minimum of R10 above the roof deck (you are in climate zone 4C), at a total center-cavity R of R49:
http://publicecodes.cyberregs.com/icod/irc/2012/icod_irc_2012_8_sec006.htm http://publicecodes.cyberregs.com/icod/irc/2012/icod_irc_2012_11_sec002.htm To get there most cheaply with something that is still remotely walkable would be 2.5" of Type-II EPS (1.5lbs per cubic foot density, R4.2/inch). For R10 that would run about a buck a square foot for virgin-stock, but about 25-30cents/ft^2 if using reclaimed foam from commercial roof demolition. Using 2 layers with staggered seams is better than a single layer, due to seasonal & temperature related dimensional changes opening/closing gaps where the sheet foam edges meet.
With 3" of exterior foam (R12.6, if EPS) you could then drop to standard density R25s between the rafters and still end up at ~R38, but since the rafters would be thermally broken by the foam above, it would outperform R38 between 2 x 12 joists. If you want to take it up to IRC 2012 levels you could put 4-5" of polyiso above the roof deck, with R25s between the rafters. Kraft facers on the batts would be fine.
Reclaimed foam is really cheap, if you have a local source. I have several reclaimed foam vendors large & small in my area (eg:
http://www.greeninsulationgroup.com/ ) These folks ship anywhere in the US (for a price) if the quantity warrants it:
http://www.nationwidefoam.com/