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I had much rather see a bald head than a bad combover! Women are NOT attracted to that! I have always thought Captain Stubing on Love boat was sexy!! Why can't they see that? I do not get it!
No. I wouldn't. He already knows he has a comb-over. He's creating it himself. If it's affecting his life negatively somehow he'll figure that out. Otherwise, if this is how he's happy, I don't see the harm. It isn't as if he's about to accidentally step into a vat of hydrochloric acid or has a giant hole in the front of his shorts with his junk hanging out or some other imminent issue. It's a comb-over, not a fashion "great" but who's fashionable all the time?
He is keeping that hair for a reason. It's his reason. If he ever doesn't have that reason anymore (or if eventually he doesn't even have enough hair to comb over), then that's when he'll change things.
When I was younger, my hair turned from blonde to dishwater and I started lightening it (it didn't take much to do this, single-process, easy) to blonde. My sister used to periodically check in with me to let me know how BAD it apparently looked. I looked cheap, I was obviously "faking it," everybody would know I wasn't a "natural blonde," men weren't going to take me seriously, my hair was LIKE STRAW ZOMG, I looked like I lived in a trailer, blah, blah, BLAH. Well, you know what? I never had a single issue directly stemming from being blonde. I got jobs. I was a parent. I had boyfriends and then a husband (and then after a divorce, my second husband). Didn't lose friends over it. Didn't lose sleep over it. I had as little or as much fun as I'd have had any other hair color. Life was as difficult or as easy as it would have been even if I'd been a "sooo much better!!" brunette.
Then one day I decided to go dark...really dark. And OH MY GOD I LOVED IT. I've been coloring really dark ever since. And I look better, facially. I can see it. And you know what? So what? LOL. I LOVED being my "cheap" (????) blonde that never negatively impacted my life in any way and now I LOVE being brunette. Leave people alone even if you think they could "look better" some other way. The OP's friend isn't going to go, "Oh my god, I totally didn't realize I have a comb-over or even if I did, I had no idea anybody could tell." He knows. Let him come to his own conclusions, whatever those may be.
What I'd tell him (if anything) is that if you're balding, you can do whatever you damn well please with your remaining hair, as long as you don't make any inevitably failing effort to conceal the baldness.
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I like guys with shaved heads myself 
