I'm sure there are good guests who ask for discounts. However, 100% of the guests I accepted who initially asked for a discount turned out to be terrible. It's a very small sample size, but is backed up by the experience of many other hosts.
So it's a no from me for anyone asking for a discount.
A guest who asks for a discount will be annoying and leave you a bad review. Same for guests who ask a ton of questions, most of which are already in the listing details.
Definitely a no. Cheap guests have always been an issue. If they are willing to spend on everything else on their vacation, they should be willing to pay standard pricing. There is also they risk they try to get money back on the backend too by making up false issues and complaints. NOT WORTH IT.
My guidelines is that I don't ever cater to random people that ask for discounts. Returning guests who had no issue? Sure. But if a complete stranger messages me and asks if there are "any discounts" I decline and reject their inquiry.
I regret every single discounted stay I have ever done. There’s something about bargain hunters that makes them the worst possible guests. Don’t do it!