A comment on board 50: it looks like you are using an original board 50. The reason I say this is because you are missing a number of woods half hexes on the south edge in this orientation, as is my original board 50. Hexes T10 and V10 (and H10 and J10) should be woods, as they are in the SK and vasl versions. I can't tell how yours are printed/cut, but on mine you can barely see a sliver of woods in T10 and none in V10.
I have not played this, so all of the following is only speculation based on your playing and some study. Regarding this particular playing of "To the Matter Born" I agree that the force going out to meet the 5-4-8s is understrength. My suggestion for the given defense would be three kangaroos carrying four squads total. The lead kangaroo of that group carries the 9-2, 1.5 squads and perhaps the MMG, perhaps a LMG. The game is over if that kangaroo bogs with the Passengers aboard. I think where I think your playing goes pear-shaped is on turn three. At the end of turn three the Scots end up in O5. If the lead group (in my suggestion, the 9-2, 1.5 squads and (?)MG advance to N5 instead (CX), they can assemble the MMG (if that is chosen) on German turn three and move on turn four to L4 and either advance (still concealed) to k4 and/or k5 or remain in reverse slope in L4. Potentially the the squad could deploy, putting a halfsquad each in k4, k5 and L4. Or perhaps the squad does not deploy; I haven't decided which choice is best. What I am sure of is that the lead group of Scots need to be at the far end of the hill after turn four and not the near end. The contents of the second and third kangaroos (with no leaders unfortunately) will seize the near end of the hill.
Of the three kangaroos climbing the M5 hill on the first turn one ends up in T9 but rather than having the second in U10 like you did it can end up in S10 in Motion. During the second turn it unloads in S9 and the third unloads in T9 I think. They then push on to the O5 area.
Unfortunately I think there are some German moves that make it possible for them to threaten the near end of the hill. If a group with leader sets up in V2 it can move to Q3 on turn one, O4 or P4 on turn two and potentially seize the O5 area before the Scots get there. That would be awkward, and might require that the Scots drop off a halfsquad, sending only the full squad and 9-2 forward to meet the paratroops. The Germans can potentially deploy their 5-4-8s, and could perhaps overwhelm the lead group, so the lead group has to be ready to fall back almost immediately.
Overall I agree it is tough to get right for the Scots and could easily be hard for them to win. I think it will be helpful if the Scots meet the Germans coming up the far end of the hill and not the near end, but I am unsure if that is enough to give the Scots a chance. I think it is a tricky scenario to play "on the fly" and needs some careful planning to maximize the Scottish first moves. Every MF/MP seems to matter a great deal in those first moves.
I'm having some second thoughts; perhaps a halfsquad, MMG and 9-2 into n4 and the full squad into L4 might work. Or the full squad in n4 and the halfsquad in L4?
JR