Might snag my first IWC - 41mm Pilot's Chrono

Hello, big watch person, longtime IWC fan, but I've yet to buy one. That may be changing this week. I have a couple of minor concerns I was hoping for some thoughts/insight.
My AD whom I have a long relationship with is willing to do 18.5% off the watch. I'm going for the 41mm in blue on the bracelet because I love it and have loved these pieces for years and years. IWC does lose value in the secondary market more than some of the other brands I own and while I don't plan on selling this piece you never really know what the future holds. Is the 18.5% discount a reasonable discount or do I need to shop around for a larger discount?

Next question, I've seen a few photos of rubber straps for these watches, some of the rubber straps don't adjoin the case, they're simply straight across (IWCs straps seem to be this way) creating a gap between the case and the rubber strap. I'd like to grab a rubber strap as well but preferably one that is cut to align with the case itself. Any recommendations?