Advice on Everose pricing, negotiation, and when to buy

[catsmeow]

Looking to the experts here for some much wanted advice about pricing, and more generally, what and when to buy.

For my first Rolex--and high-end watch in general--I initially had my eye on an oyster perpetual, SS with blue RN markers, 31. It seemed like a good fit for my budget and lifestyle.

I popped into an AD to see if they had it, but they did not. Sadly, my eye strayed to the case and came upon the TT Everose datejust 31 with the fluted bezel, Jubilee band, RM, and white face.

My heart jumped. It's truly a gorgeous watch. Sadly, it's also more than twice what I had intended to spend, leading me to wonder:

a) How much wiggle room do I have for a watch like this? I've tried negotiating the price with a few ADs, but haven't been able to knock off more than 7%, excluding taxes and shipping.

b) Is this something that would reappear on the pre-owned market in 5-10 years?

c) Is it worth getting my original model and waiting to upgrade? The benefit of the oyster was that it was really understated, and I wouldn't be as worried about it getting scratched at the gym. With the Everose, I'd worry about damage, and inviting unwanted attention.

Thanks!