The conditions in the video were not particularly rough and did not have consistent waves, just chop. There didn't appear to be substantial wind, either.

When waves are steep and well-formed, the boat will broach and every wave will pitch the paddler sideways. Cowboys become extremely unstable and paddle floats tend to flip the boat.

If one has a buddy nearby, why would you self-rescue in the first place? That makes no sense as an assisted rescue it typically faster.

The side-entry re-enter and roll is an easy rescue to learn and it doesn't actually require the ability to roll; you just have to have a competent high brace or sculling brace. The name really isn't precisely descriptive of the technique. When combined with a paddle float, it can be accomplished without even submerging. I've done it many times in practice and when teaching it, in a variety of conditions. As I said before, this is NOT the inverted reenter and roll one sees in books all the time; it's a much easier variation on it.

A paddle float rigged on the boat is a liability in steep waves and won't help you pump out; it's more likely to pitch you over. The best course of action if is to try to get to calmer waters or to shore. While poor deck rigging can make a paddle float rescue difficult, it's not actually required, as many people perform them by holding the paddle against the coaming.