Yes, I don’t need to haggle, I just put in the dates and click book if it meets my criteria…
Digital Nomads
So, no?
If you don’t have any reviews on Airbnb you might get rejected. If your discount is too big they might reject your request as well.
Go for it
Be respectful, polite, complimentary
AirBnBs aim for 40% occupancy so your theory is bang on
Book a place for a few days, test it out, if it works out drop the host a message - not via the platform, mind, do it via WhatsApp or something, a lot of them give it to you when you arrive to facilitate comms - and ask to extend your stay and pay via cash/bank transfer/credit card directly with them.
I secured a decent enough place in Mexico City like that and even got some discount as host doesn't have to charge to make up for the loss via AirBnB's own cut.
I booked a month once for around 900. Ended up staying a lot longer. He offered that I could just pay thru Venmo and ended up only charging 700 for the rest of my time there. He has multiple properties so I just txt him when I come home to visit. Once you build a little trust it’s easy to cut out the middle man.