I've seen worse houses than yours in MA- trust me!
I recently saw a raised-ranch just outside of 128 with similar issues at the cantilevers, but worse yet, it only had R8 econobatts in the 2x8 ceiling joists below the attic half, and who knows what (if anything) is between the 2x6 rafters in the cathedralized ceiling half! (I advised my friend to not buy that one.)
If the facers on the foam are in contact with adjacent layers it doesn't matter which way you orient the facers.
Kraft facers on batts are not vapor barriers, but batts need air barriers in contact with both sides of the batt. As kraft facers acquire moisture they become fairly vapor open (5+ perms), whereas when dry they're about 0.5 perms. A 3/4" plywood or OSB subfloor is already a pretty good vapor retarder, between 0.5-1 perms. As long as the cladding on the under side of the cantilever is more than 0.5 perms there isn't a vapor diffusion path to be concerned about, but if there isn't an air barrier where the joists cross the foundation there can be a fairly significant air-convection movement of moisture to the band joist and the bottom cladding of the cantilever.
Ideally the plumbing would be all COMPLETELY inside the pressure & thermal boundary of the house. But given that the ideal isn't possible without some re-plumbing, how much space is there between the pipes and the bottom of the cantilever bay, and how far from the band joist?
The stack up matters, since foil facers on rigid polyisocyanurate are true vapor barriers. It's not totally clear where you intend to place the foam board relative to the batts, or the rest. It sounds as if you're going to apply the rigid foam to the underside of the subfloor over the cantilever, and fill the rest with R30 batt(?). Or are you only talking about cut'n'cobbled Tuff-R as the air barriers where the joists cross the foundation sill? Or is it something else?
If the facers on the foam are in contact with adjacent layers it doesn't matter which way you orient the facers.
Kraft facers on batts are not vapor barriers, but batts need air barriers in contact with both sides of the batt. As kraft facers acquire moisture they become fairly vapor open (5+ perms), whereas when dry they're about 0.5 perms. A 3/4" plywood or OSB subfloor is already a pretty good vapor retarder, between 0.5-1 perms. As long as the cladding on the under side of the cantilever is more than 0.5 perms there isn't a vapor diffusion path to be concerned about, but if there isn't an air barrier where the joists cross the foundation there can be a fairly significant air-convection movement of moisture to the band joist and the bottom cladding of the cantilever.
Ideally the plumbing would be all COMPLETELY inside the pressure & thermal boundary of the house. But given that the ideal isn't possible without some re-plumbing, how much space is there between the pipes and the bottom of the cantilever bay, and how far from the band joist?
The stack up matters, since foil facers on rigid polyisocyanurate are true vapor barriers. It's not totally clear where you intend to place the foam board relative to the batts, or the rest. It sounds as if you're going to apply the rigid foam to the underside of the subfloor over the cantilever, and fill the rest with R30 batt(?). Or are you only talking about cut'n'cobbled Tuff-R as the air barriers where the joists cross the foundation sill? Or is it something else?