I usually just work it out with the dog owner for a mutually agreeable time. So far it's worked out OK for our family. The sitter we use for our dog through Rover has a "starting time" for the day, might be around 8:00 am. If I need an earlier drop off, then she charges a bit extra ($5 or $10 I think). She watches multiple dogs and this is her primary source of income, so it works for her. As a pet owner, it seems fair.

Have you considered offering a http://Rover.com branded hat for walkers and dog sitters to wear? I could easily through on a baseball hat while walking dogs during the day. A bit more likely than changing shirts. The bright green would stand out for sure.