He should think about doing a fixed wing PPL first, in order to assimilate basic skills at a lower cost and level of complexity He can then step up to a PPL (H) on a Robinson or similar
NVFR would probably be a minimum requirement, but IFR is an extra step up again - I'd recommend taking the Jag if the wx is $hite
If, as it sounds, cash is not a major obstacle, he would be better off with as many helicopter hours training as he could get. Why learn on planks if he has no requirement for a plank licence?
As for NVFR and IFR, on a privately operated helicopter, on a newly issued PPL(H) licence you'd be biting off an awful lot. He'd be better off getting a PPL(H) and a pilot. May cost more, but he'll live longer to spend what remains. Try reposting in Rotorheads forum, you'll get more advice than you'll know what to do with!
P1