Hey Sonny Dong! When giving access to your cleaner, there are a couple of options. You can get a lockbox and keep it next to the water sprocket outside for their access or get a keyless entry so they can have their personal code. Plus, your able to track every time someone opens and closes the door. Now for the rental insurance, was it first mention on the lease? If its a month to month lease, you can make the amendment to the lease. If its outside of the that, you would need to wait until the lease is over from my understanding.
I would keep the utilities under your name because if he/she doesn't make the payment who do you think is liable if its under your "primary tenant" name..? Its definitely not going to be the primary tenant. It would be best if you manage everything yourself instead of relying on a tenant. Your primary tenant should be your eye's and hears of the household, but I wouldn't give them duties of your responsibility.