What does the DOD regulation say about recording daily activities for YouTubers/influencers AKA entertainer money?

This is not regulation but a link I found that's a discussion about those in uniform who are influencers who make money and it seems like the DoD maybe needs to update regulations to address the realm of social media influencer while on active duty.

https://prsawesterndistrict.org/can-military-influencers-ethically-use-their-status-to-sell-services/

I concur that you should definitely go talk to JAG at the closest base to you (since your profile says your Guard) to see since it seems to be grey area - and even more so if you're Guard/Reserve it may be.

I'd say talk with PAO and JAG

You cannot monetize any of portions of your duty. I have seen this from an "influencer" that was selling products but also had photos of her in uniform on the same IG page. There is a Drill Sergeant that tried and if you watch him now, he wears his older uniforms that are not worn today. Do you have a page?