Hey folks! Forgive me for asking some noob questions

Reaching 30 and looking to give myself a decent gift (or two…)!

Looking at Datejust 36 silver dial, fluted with jubilee and Yachtmaster 42 white gold (or potentially AP Royal Oak which seems pretty impossible to buy for a first timer?! any insider info welcomed!).

The DJ 36 seems like a pretty versatile watch for different settings, can be easily dressed up/down.

The Yachtmaster 42, love how graphical it looks. The matte black bezel with polished markings, bold face… mmmm… It seems to be a watch with more characteristics. Then I did a search on this sub and didn't see many posts about this watch. And sensed some hatred toward YM in general? I like the watch but also don't want to turn this into a bad investment if it is not a well-regarded watch in aftermarket.

Then it comes the actual buying process. Are both Datejust and Yachtmaster considered hot watches that I need to get onto the waiting list asap? Any dis/advantages of buying two watches together vs separate (possible discount etc…)? And is the 'asking for the tax off' a frowned upon thing to do with Rolex ADs?

I'm looking to purchase through an AD. Located in Toronto, Canada. Any AD/SA in/around TO you would recommend in particular?

Thanks in advance for your help everyone!

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