I take care of a diabetic kitty who also needs insulin twice a day. I was specifically asked because I used to give Morgan shots. I won't board Morgan because stress causing the sugar levels to rise, and being away from home would be such a traumatic experience for him. When he was still taking the shots, I made sure that anyone that I may need to ask to come to my home to watch him was familiar with administering his shots. For my diabetic kitty, boarding is not an option. Especially since he is now regulated with food, I don't want to disrupt his routine in anyway and risk getting back into the shot giving. Just another side of the equation to think about. I would personally be much more comfortable with an experienced person like yourself coming to give my cat medications while I was gone than Joe Blow petsitter. Who is to say that something doesn't happen to one of the cats you are watching even if they aren't on medication. What would the difference be?