Can I send multiple quotes to a customer?

This would be helpful if they are considering a stay from Wednesday to Sunday or Thursday to Monday.
Alternatively
Send them a tool where they can play with what is entered to get the dates and rates that they want.

Yep, create as many quotes as you want.

If you want to let the guest experiment, use the booking widget on your site or give them a link to one: https://www.ownerrez.com/support/articles/widgets -- that will give them a live quote as they update dates and guests and let them initiate a book now if you have that feature enabled.