See there is an issue using the old measuring sticks. Used to be going gold meant a band MIGHT start to make some money but not necessarily "FU" money. That is why bands toured so much because there they could actually make some good cash if they got popular and sold out the big venues. Otherwise the record companies made the big bucks off of the music sales and if they snookered the song writers out of the publishing rights the band rarely made anything substantial on music sales.
Now anyone with 10K in funds (or less) can make a very professionally sounding album with a knowledgeable operator/engineer. So you can produce a good product for a very small fraction of what it cost in the era when record companies controlled the process. You can create your own publishing company and you can distribute via the internet either digitally or with physical media via Amzon etc. The problem is everyone can do it and thus your awesome CD is lost in a vast sea of every other band doing the same exact thing.
BUT, you get much more money off of any music sales you do manage. used to be if you got pennies for each unit sold you were considered very lucky. Now you can easily get over 50% of anything sold. So now you don't need to go gold to make some serious money. If you sell 10k copies of a CD that retails for 9.99 you can profit over 50% of that. And at that you won't even show up on the billboard charts likely but a two man group playing live 9 months a year on a circuit and selling 10k in album sales can make some very good money.
Now Daryl does a show called Live from Daryl's House. Which BTW used to be exactly that. He would get some guests musicians and broadcast live over the internet from his house. He started small and now it is a big endeavor that is also broadcast on MTV though now it is from his club. So yeah he is playing live all manner of material some new some old lots of it his guest's material and is making some serious scratch. So he is not a nostalgia act but more a music variety show that broadcasts via the internet.
Publishing rights on old hits will still bring in money when they are played on radio/tv/movies/commercials. Decades out.
Play a live show and you have to again tomorrow and the next day and so on for decades out.
I don’t know that the shed amphitheaters would be booking him if he turned his back on playing his old songs live (as Bowie did for awhile).
I agree as a musician he’s not a nostalgia artist, but to the livenation bookers and majority of the audience he is.
I saw Bob Dylan last year (4th time). I knew the setlist going in (looked it up online). Almost nothing from the 60s, a couple from the 70s, and heavy focus on his last 4-5 albums.
Band and voice sounded great. Bob played quite a bit of harmonica even. Crowd I talk with later (including people I knew) were disappointed by the choice of material.
I’d taken the time to familiarize myself with the songs on the list.