What platform are you on? Smoking man always shows up for me even if it take 7 minutes. Have you tried ICA Safehouse start vs Main Square, and letting intro play vs not to see if there’s any difference in his cycle?
Other than that, you might just have to take advantage of the SA bug and emetic poison his coffee right at the start, then come back later and hatchet him in a toilet. I don’t wanna remake it now that I’ve posted it on Reddit too (and had it recreated on all platforms) plus there’s no delete feature. What platform are you on?