My previous sitters are unavailable and I don’t have a sitter lined up for an upcoming trip. I’ve never done the option ‘Invite To Sit’ until now. I reached out to someone who is local. Can/should I reach out to multiple people at the same time, or wait until I hear back from the first person?
Invite to sit seldom works. If you don’t mind probably wasting the time, you can try people who are beginners and local to you (who may be anxious to get reviews), or anyone who has favorited your sit.
Your better bet is to make your listing more attractive. If you connect it here, some folks will be happy to take a look at it for you.
How long until the trip? If it’s seven days or less, you can also post in the Last-Minute Sit forum here.
As @Val said, sit invites have a low success rate. This is a very frequent question, and there are many existing threads about this topic. Here’s some:
Making sure your listing is as attractive as possible is key - here’s how to link your listing to your forum bio for members to view & give feedback. How to add a listing or profile link to your FORUM profile
You might also want to give this blog a read to ensure your listing is as attractive. Hope that helps! 
I’m in Wake Forest, NC and my departure date is Friday, August 9. My original return date was August 18 but I did check the box for ‘rough dates’ because I would like to be gone for about a week longer if the arrangements worked out. I would even consider a partial sit and work around that.
Do you mean that’s another piece of information that owners have to fill in and sitters don’t get to see?
As a sitter I am not aware of any specific box for that. I’ve read, usually in the headline, flexible dates or a specific description as you have written here.
Hey, RMRL…you can definitely list that at Last-minute sits.
I’m not sure what sitters can and can’t see. I never noticed the option until today.
@RMRL Unfortunately sitters can only see what an owner manually writes on their profile. They cannot see ‘tick-a-box’ information that was filled out by the owner. I suspect that these ‘tick-a-box’ options are for THS data collection purposes. You can always view what your listing looks like to sitters by clicking ‘view & edit listing.’
I used it, and it was a sitter who had applied for my sit 6 mos prior. So, we had a zoom call already. I think you should do one at a time. If your in a rush maybe put
" please let me know if it fits with your availability, as I need to talk to someone soon"
If you don’t hear from them, maybe you can withdraw it and send another?
‘Invite to sit’ might be useful if HOs could search for and invite sitters that have indicated they would like to sit in the HOs area.
But this is not a feature and there is not a filter for that.