When I’m thinking about Dan, then I’m not sure he feels you’re speaking to him by calling him a “smart business owner”? I also feel this headline is perhaps a little too generic. What’s the benefit of the copywriting hacks? How does it make life better for Dan?
Regarding your fourth headline: Does Dan have a “social media strategy”? I’m not sure. He doesn’t seem to be the guy who talks about strategy much, so this may not work?
I like your second and third headline – and these I’d say definitely appeal to Dan. The words rookie and making you broke are great power words.
By the way, I’m not sure you need the word you twice in the third one. What about: 7 Warning Signs That Creativity is Making You Broke (or Go Broke?)
Enchant readers. Woo customers. Win business.