66 hand - I generally call 3b if I'm getting > 15x effective. I think overall this might be slightly -EV, but I'd rather expand my calling range a bit IP there and make their life difficult being OOP deep'ish.

AK hand - this seems like a reasonable spot to raise to $35-36 or so to iso the shorty (and is a spot you're never bluffing, since he's already all-in), and if you face heat I would fold.