thank you all for the responses :)
I find my cat too is very forgiving about the nail clipping. It is misery for her, but when she's done she gets a treat and playtime and all is forgotten
My cats are indoor cats so I only take them if they get sick or when they need their shots. My vet calls to remind me about shots.
I've always clipped my cats nails myself. 2 of them hate it and one is ok with it but none of them resent me. Once I'm done the 2 that hate it will ignore me for about 10 min but then it's back to business as usual. I doubt you really have to worry about that very much. If you're not sure how to do it then have your vet show you at your next appt.
Ideally, every six months for a check up. Annually is fine if there are no health issues or problems apparent.
Otherwise... I would suggest having someone else do the clipping, as it will keep kitty from resenting you, should he take a strong dislike to the process. I would get a good reference though, and make sure whoever you use is licensed and insured.