Tips about leaving my cat in someone else's care.

My family is going away for almost 2 weeks later this week, my friend is house sitting to take care of our cats. I'm worried about my almost two year old cat who's never been left home without any of our family members, my cat has seen my friend a few times but they've haven't necessarily interacted. I'm worried about how he'll react to all of us not being there. He stays outside during the day and comes inside at night. I'm worried with a kind of stranger staying here he might run away or freak out that we're not there. Is there anything I can do to help him? 

Can you have your friend come over and spend some time him before you leave? It would be a good idea to make sure he will come in at night for your friend.

She's staying over tonight, we're leaving tomorrow. 

Do you have cameras in the house to check up on the kitty and your friend?  I would seriously get a camera for every room so you can monitor him and his care.  I would go to Walmart or Home Depot and get something affordable.  People tend to be on their best behavior when they know they are on camera.  

I have a house sitter come to my house and stay here.  I've known her for a long time.  My girls don't really interact with her much; but I leave her written instructions and info letting her know what the girls normal routines are and we keep in touch via text while I go away.  My 2 are on meds so its become extra important.

As for comforting the girls; I try to leave out an unwashed t-shirt or two that I've worn.  They have their usual sleeping spots and toys out.  

They have always been fine.  They come to the house sitter to get their food and treats (which have their meds in them) and are glad to see us when we get back.