Sure if you're only looking at his money/material possessions.
But Dave also is a person who is completely unfulfilled by what he's obtained in life. That's why he has to flex on twitter about "muh famlee" constantly at 3 AM after a bottle of gin.
Dave objectively has no future, ya think he's gonna be streaming when he's 65? Gonna unbox his first social security check? He's got no marketable skills that will help land him a job after streaming and an employer that google "Philip Burnell" is gonna get a picture of him jerking off.
He has no savings and no plan for his retirement, besides probably trying to live off social security which will not be anywhere near enough to sustain the lifestyle he expects. He's one medical emergency from complete financial ruin and he's got a myriad of health problems looming. I doubt he's been to the dentist in years so who knows when his teeth are finally gonna give out, ain't gonna be able to afford the thirty grand dentures that Boogie got.
Basically, while Dave might be ok for the moment, he's fucked.