No, it's not really possible to do that today with our site. The closest you can get is to put in a bunch of quote requests for the dates you're interested in and then just come back on daily basis and click the links to view your quote which will prompt you to refresh the pricing. Then you'll get a new email in a few minutes with updated discount rates for that period.
Triggered email alerts are only sent based on existing reservations that you are tracking. There's no way to enter a bunch of hypothetical reservations and be alerted on those, unfortunately.
As for our website design, it's was done about 10 years ago when we first launched. We're well aware that's it's pretty long in the tooth. We're a few of weeks away from launching a refreshed mobile-friendly design so stay tuned!