It depends on the percentages. I think you want to consider who will get the first open shot. If you do the standard safe from the break, I think the chance you will get the first shot is less than 50%. If you can break in a ball 55% of the time, that seems to give a better result.I haven't seen the video so I'm making the assumption that pocketing the head-ball in the side would open the rack a lot more than the standard safe-break. So if you miss that shot, you're not just losing control of the table, but giving your opponent a much better opportunity to get rolling, aren't you?
If the safe breaker got the first shot more than 50% of the time, then it would clearly be to his advantage to break. But I think we don't know what the percentages are.
A similar consideration comes up all the time during the game. You are facing a shot that feels about 70% for you. Should you play safe? If you are only 50-50 to get the first shot after the safeties start, you should shoot the 70% shot. If you are 100% to get a 90% shot out of the safety battle, then play a safe. My conclusion is that in general you should go for 51% shots unless an absolutely inescapable safety is at hand. If you played such a safe on Lassiter he would take three, play safe and you would be stuck on the end rail with no reasonable safe to play. You would net 15 points and give up a couple of racks.