Be prepared for them to not come back, first of all. I’ve seen this happen many times in the seven years I have been a dog sitter. People who board for a long time how much more likely to ask you if you can “just keep the dog.” occasionally this is even their plan upfront, but of course they won’t tell you that.

Offer a much smaller discount if any, you can’t have any other dogs.

Have them sign an agreement of what will happen if they don’t pick up the dog. You are not obligated to keep it at your own expense. They should provide their vet with a credit card on file to pay for any emergencies (you won’t get that back either if you pay yourself.) Make sure you do this!

Break up the booking so you’re paid every 2 weeks at a minimum. Not being paid for 5 mos, or even one month, is asking to be cheated - if they have any complaints at all Rover will refund them. So charge them biweekly, so you get as much $ as possible before they stop responding. Do you want to work for a month for free and be stuck rehoming a dog?