Should I do drop in visits at 10pm?

I would only schedule a meet and greet during daylight hours. All my meet & greets start outside. I advise only go inside the home if everything is progressing well. There are other sitters who also don’t have anyone to go with them. One way to handle that is tell someone when & where you’re going and ask them to check in with you by phone at a specific time (maybe approximately an hour after you arrive there) or that you’ll call them by a specific time.

If this client and dog is a match, and you’re comfortable walking in that neighborhood when dark, I would not have any problem giving a dog a walk at 10 PM. My dog and many dogs I know who are trained to only relieve themselves outside (not using potty station inside) usually has the last walk of the night at 10 PM or sometimes later. I see you wrote that she wants someone to “let the dog out “. I would clarify exactly what was meant before even agreeing to meet the person. While I will walk with a leashed dog at night, I absolutely will not accept any assignment where I’d be responsible for any pet being off leash. Rover won’t support you if you allow a dog to let itself out on its own and one of many possible tragedies befalls it.

If you are not comfortable walking in this neighborhood, but like the dog & the client, another alternative you could propose would be to offer a modified version of “boarding” or night-time “day care” where the dog stays at your home while they’re away and gets that late night walk in your neighborhood.

ADDITION: Boarding is defined by rover as up to 24 hours in the sitter’s home. Day care generally is for 8-9 hours in the sitter’s home. If you only offer boarding, but want to create a slightly reduced rate for less hours, you can do so by booking as Boarding with a Negative (-$x) “Cost Adjustment”. For example if your boarding price was $35 and you wanted to offer them 8-10 hours of care for $25, you’d book it with -$10 cost adjustment. Of course, you’re not obligated to offer this. I’m thinking if they regularly need the service and you like their dog , this is one way to handle that costs a little more than a walk but less than boarding, which would result in frequent consistent bookings. While that costs more than a walk, the dog’s health/safety/well-being would be much better protected, and hopefully they’d understand that. BTW: It appears “you’re away” in your rates section.

I wouldn't do it without meeting the person. Also you could ask if it would be okay to bring someone with you to the booking to make you feel safer.

Trust your gut for sure, and do what you need to feel safe. As a counterpoint to some of the other advice offered, I'll say that I also work evenings at my "day" job so I often end up doing drop ins for clients who are out of town at 10PM or later. I specialize in cats, so these drop ins are usually just food/litter box visits. Right now I'm housesitting for four dogs and a cat and they have a fenced backyard so I don't have to worry about walks. But it's all about your comfort level. If something seems off, don't book, but just the late night request itself isn't a red flag for me.

Is that past your bed time? Do you have to work the next day. To me late hours like that would be a higher rate. Drive time, gas, personal time. Not like any other service does that. If I asked a venue for access to set up a party over night instead of am business hours they charge double the strike time fee. I see so many sitters giving away services for next to nothing. This is a private, pampered pet service that is outside the traditional brick and mortar doggie day care and boarding. If they are charging a $75 day rate with lots of rules and regulations, we should be $125. We are liable for everything and Rover ins only covers the clients dog. Not ours, not our property!

I do late night visits, but i do meet and greet first during the day. Some of my clients work nights or weird hours at hospital, so I don't have a problem with these visits. I carry some protection on me daily and nightly though.

Always always trust your gut. Read the book The Gift of Fear and always trust your gut. It gets information ahead of your brain on dangerous situations. Put a cut off time for overnight drop offs on your profile.