You're high on meth if you have 2-3 kids and spend almost $5,600/mo on rent with a $200k HHI. It's feasible for a single person, but most families making that much would not be living in Manhattan. NJ or one of the outer boroughs will get you a decent place for like $3,500/mo.
xetmes
Bad examples. Ulysses Nardin are some of the most hideous "high horology" watches I've ever seen. B&M are meh and any somewhat desirable Chopard or Bucherer is more than $5k. Bremont charges ridiculous prices for basic ass ETA movements so don't get me started on them... Popular watches are popular for a reason.
Buying new from a Japanese dealer. You can find them on Chrono24 for around $4200 + shipping/tax/duties to the U.S.
Grand Seiko SBGH273. I priced it out to around $4800-$4900 shipped with duties included from Japan.
You want a vintage one specifically? The new reissued Willard is less than $1,000.
Mechanical watch accuracy doesn't matter as much as warch dorks make it out to be. Half the time I don't even bother setting a watch before I leave the house. I have the time already on my phone, in my car, on the wall at work, on my desk computer...
Datejust because those shark tooth hour markers look goofy as hell.
Get it regulated or try doing it yourself.
Longines are glorified mall watches.
I'm a big fan of their Flieger Pro and how you can really customize it to your liking.
Use /r/Watchexchange. If you're in the states, you can ship with USPS flat rate boxes.