With regards to the T-1 vs T-44 . . . yes, the T-44 is an old POS. Yes, most things are done old school. Yes, our GPS/FMS only works about 1/3 of the time.
However . . . perhaps due to my lack of breadth of experience, but I've never met an IP who says it's easier to go from new -> old than from old -> new, civilian or military. EVERY IP in the training world, T-6, T-37, T-44, T-38, T-1(not as much exp with the last 2) talks about how much easier it is to teach the fundamentals and "old school" methods and THEN transition to the fancy-shmancy GPS, FMS, FDI, etc etc. Perhaps that's just their nostalgia talking, but I'm inclined to agree.
Sure, most of the emergencies you practice in the T-44 will never happen, and they likely won't happen in the Herk either. Sure, you'll have a nav, eng, etc etc. And if you're in a J, H3, etc, you'll have all those modern avionics to help. But what if something does go wrong? What if you have a weak Nav or copilot who can't work the technology right, or who makes a lot of mistakes? That is where it seems that the ingrained knowledge of instrument procedures, dead reckoning nav, and solid SA will save you, and that's what Corpus teaches. You can know a shit-ton about FMS operation, but if it breaks/malfunctions/etc or your crew isn't strong, that tech know-how won't save you. The old-school methods will.