httpswww.gregthomason.c

It sounds like you are changing companies, which I'd do as well. My professional insurance is through The Hartford. As William points out, if you are not a professional photographer, traveling for work, your travel insurance should have you covered.

Bjorn, there are several ways to get that gray. If shooting a closer portrait, I prefer to have a white background and let the light fall off (inverse square law) do its thing and let the bg fade to gray. On larger portraits, such as this, the light fall off may work, but keeping shadows off becomes more difficult. Getting a gray background and lighting it independently from the subject may be they way to go then. As others have said, have enough separation that the subject's lighting and shadows don't influence the bg.

I will echo many responses here and suggest Model Mayhem. If you're willing to pay an agency, then going through a local agency is a sure bet.

Master each strobe and modifier individually. Self assign tasks such as one light portraits. Once you've got a feel for one light, start using two, one key and one fill. Try using a soft box as key while using an umbrella as a subtle fill. Don't worry about more modifiers or the grids, until you're comfortable with what you have.