Agreed, business class flights are more than enough
Cars are the poorest investment there is, I only have one if I really need one and currently my lease is paid for by work as I have a car allowance as part of my pay package. Nothing but an egoistic exercise, you can still drive a nice BMW 325 is a nice enough quality car anyone needs or an Audi A5 Sport or a CL merc...etc Bentley and super cars are for people with too much money where you run out of ideas where to put it.
Watches I'd say keep it under $10k, but no harm if it becomes a hobby to collect them as they hold their value very well should you need to liquidate.
I can see a CL550 instead of an S550. I just named the S550 because it's about as.. err.. I dunno "posh" as you're gonna get, and it's about 1/2 the price as a Bentley/Rolls.. actually, you can get a pre-owned 2014 S550 for about $110k well optioned.
.. and you can get a pre0wned 2014 CLS550 for $80k.
"preowned", but still only have about 5k miles.
shit.. he can get a 2013 Range Rover Supercharged AND a 2012 CLS550 for less than $200k (probably less than $170k)... and still pay $1k per month less than the lease on a 2014 Bentley (if not $1500 less).. that $1500 would cover 2 mortgage's on 3000 sq ft homes in Arvada.