Thank you so much for the quick feedback. I looked up most of the issues on ebay, but the sold listings range so much for both ungraded and graded, I figured I would come here to ask because the sheer amount of keys sold on ebay make it very hard to pin down cost of grading vs payoff calculations. I wasn't sure if there was like a rule of thumb. Mostly, I just don't want him to get screwed by some unscrupulous vendor who claims they are in worse shape then they are, and since neither of us is a qualified grader, some of the more valuable issues definitely worry me because he has been scammed out of some of his keys before.
For some of the more valuable issues I'll upload some pictures in the thread you mentioned @Get Marwood & I and see what happens. @joeypost We are learning towards grading them, but this process is just foreign to us both. We have both only ever swapped or sold basic issues locally, he has never looked at selling his more valuable keys before, and want to make sure we are doing things right.