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When the singer can't sing any more.

Sure BB lost some of it later on, but was still a going concern at least a year or 2 before his death when I saw him. He still had a voice, and I would have considered the ticket well worth it for just one of those BB notes on the guitar with the vibrato that make the hair on your neck stand on end. Sure I would have loved to have seen him in the 70s, but I'm still glad I did in the 2000s.
I was at one of those shows, and I brought my wife, who had never seen him.
No regrets, although I'm glad I had the opportunity to see him 20 earlier when he still had it...
 
Ouch... that performance is rough. Hoping he had a cold or something... It unfortunate when folks can't hear themselves singing poorly. I'm not sure if it's hearing related or what their brain "thinks" it is hearing. We've all been around folks that want to join in and sing, and are so off-key it's beyond comprehension. At least the OP's friend and JBJ have been on target for a good portion of their careers and either voice, hearing, or a combination are in decline. I was in a fairly small club the other night seeing Phil Vassar and band, and the FOH volume was really loud, like Alice Cooper loud. The band had IEM's so I'm not sure they realized how loud it was in the venue. We use regular stage monitors, but my ears are still telling me since Saturday night that I really need to be careful from here on out. At 65 my hearing is still fairly good, and I really feel for folks that are having issues.

The OP said his friend had tried IEM's, one thing I have in my studio might help. I bought a Behringer Micromon MA400 just to try it out, it's an mic / headphone mix amp that connects inline with your mic XLR cable and you can create your own mix between your vocals and the monitor mix. The Behringer works OK but is Behringer "meh" quality. Someone probably makes a higher quality version. Might be something to try and the singer could dial in his own mix with separate control of his vocals. The MA400 is like $30, which was why I gave it a try. We use it for our drummer, while he doesn't do a lot of singing it gives him a little more control of his monitor mix for quiet practices and recording.

Good luck with it, hope something works out...
 
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Sounds to me like his hearing aids are not optimally set up for what he wants, I use hearing aids and I got my guy to set up a musician’s channel for me, it’s slightly more sensitive and I can hear everything in more detail, it’s all fairly easy and works off an app, is it possible he could use a bit of help setting up the app for when he is playing practicing is he practicing without his hearing aids ?
 
Well, judging by the bands that I see playing in bars and clubs and ones that I've tried out for, it doesn't matter if the singer can't even carry a tune in a bucket , because these absolutely horrendous "vocalists" somehow have jobs in bands and the people in the audience for the most part don't seem to notice that it sounds like someone is strangling a cat into a microphone onstage.
I mean there are SO MANY bands with just effing atrocious singers, and I'll never understand it. It really sucks having good pitch, I suppose!
 
Donno about your guy, but my guy gets it.
He just knows he can't do anything about it, and it's as good as it's going to get. At some point the bookings will stop. B.B.King continued to tour long after his skill was gone, and people kept buying tickets. My guy's no BB King, tho...
I saw Willy Nelson a little before the pandemic. Sad. Very sad.
 
Have you heard some clips of Bon Jovi lately? He does not have it any more. Some people - amateurs and pros - don't know when it's time to quit.

I also recall that the great Frank Sinatra also failed to impress me as he continued to sing into his late 60's and beyond. At the time I was disdainful of that genre of music but now, in my early 60's myself, I wonder if I'll have the good sense and grace to give up my passions if I can no longer do them justice.

Edit: On the other side of the coin, I saw Stevie Winwood open for Steely Dan back in 2016 and he was superb, vocally. Not only that, but his guitarist was a no-go so he and his sax player swapped guitar duties seamlessly. Very impressive!
 
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Ya gotta speak up.... One on one... in private. Don't be rude, but don't beat around the bush either. Talk about getting older and not sounding as good as we used to. I just prefer the blunt reality approach the most.... Be a friend.... if I my fly is open - tell me. If I got a booger hanging - tell me. If I sound like a drunk singing in the shower - tell me. I obviously don't know...
 
I have an "expressive voice" when I'm squeezin' out a steamer as well.
Well, I suppose opinions vary about Dylan's singing, but early on, when he was having hits, there clearly was an appeal to it. The phrasing and timing with the rhythm, putting it out there with forcefulness and control, spitting out those wonderful lyrics ... yeah, there's a reason he got famous as a singer/songwriter. Later on, that all went to crap, though occasionally he'll do a good performance. That's my take anyway, and I'm not alone in it.

 
I got involved with a singer who is rebuilding a band he had until 2017 or so. He recorded three CDs between 2012 and 2016 and his voice sounds good on the recordings. But, during recent rehearsals, his vocal intonation is all over the place. So is his slide guitar playing. When I comment about the latter, he sheepishly says "I know - I'll focus better." He's 73 years old, wears hearing aids and uses a Shure headphone/mic combo.

He has 3 gigs booked beginning in early June. As an audience member, I would walk out of a performance if someone sang this badly. As I've gotten older, that sort of thing has only become more irritating, so I can't envision being a member of a band and having to put up with it.

How do you tell someone they need to do something drastic, like:
1) Work on the technology you own and see if it helps. Do it by next week.
2) Give up singing and end the band.

I'm open to other solutions. I could just walk away, but rehearsals are in the middle of nowhere, so it's practically impossible for him to attract players.
What are you trying to say?
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:)