Some dogs won't ever be okay with. My sister's dog has to be sedated. Once he's sedated, she just has them do everything from nails to shots to teeth check.
When he was about 8 months old, he got hit by a piece of sheet metal they ran over with their big power mower. The vet visit was tramatic and now anything that looks like a vet instrument or looks like a vet, he gets hysterical.
They've tried desensitizing him but he's just not reasonable about it. He hyperventilates, tries to run away, foams at the mouth and sometimes pees himself or howls. My sister calls it PTSD for dogs.
They drug him twice a year, have the mobile vet come to the house and do everything that way.
Call around to groomers, most places charge 12 to 15 but sometimes you can find a place to do it for 8.