Homeowners probably isn't going to help much. Cash stolen via break-in or individuals voluntarily allowed within your residence are covered, but there typically have low limits on cash, like a maximum of $1,000-$1,500. In can get trickier with the latter as well, as most policies include wording such as "money or valuables stolen from your home if your home/property was properly secured." What the hell does that mean? Its usually enough gray area for the insurance company to wiggle through in the event of the theft was done by someone you know and voluntarily allowed into your home.
Homeowners typically requires proof of purchase or possession, which may or may not be a path someone wants to go down, such as bank transaction, deposit slip, etc. In addition, they may require a police report, which once again may not be a path someone wants to go down.