MGW-it doesn't sound to me like H is ready to make a decision but talking about the finances may actually be a very good start. He had to know that telling his boss he would not do it her way would lead to trouble. Hopefully after you have been at this job for a while your feet will hurt less. When I went back to waitressing after taking a few years off, it took a while to not ache so much.

Talking about the finances show you are a team and that is something they face very slowly.

If you focus on the past, you ruin the future. You can only live for today.