Greetings all.

Firstly, let me apologize if you have already been subjected to my endless agonising on either "The other forum" or Instagram. My 40th is next year and I must be undertaking the most drawn out decision making process for any mid-tier watch ever...
I aim to spend around $2500-3000AUD (approx $1900-2300 USD currently) and, as a man of limited means, this will likely be the most I ever spend on a watch (except for maybe my 50th...). I'd like it to be a significant enough piece to mean something for some time and possibly be a worthwhile heirloom.

Current shortlist is:-

Sinn 356 Flieger.
I really love the look, feel and presence of this watch.
The size is about perfect at 38.5mm.
I have no real need for a chronograph but really dig the dial aesthetic.
It's a watch I feel I could wear pretty much anywhere, anytime.
Only possible negative is the ETA/Valjoux movement being available in so many watches (including many cheaper) may make it feel a bit less "special".

Nomos Tangente or Nomos Club.
Jury is out on which. The Tangente is beautiful but, realistically, I think the Club would suit my casual dress and lifestyle more - making it more versatile.
In-house movement and exquisite build quality are obvious draws here.
No real negatives. I just feel the Sinn would get more wear and may be a bit tougher?

Option 3 - The Vintage Choice.
There are a couple of options here that might just scrape into my budget incl: 60s Breitling Top Time, 60s/70s Datejust/Air King, 60s Omega Seamaster etc

This is where I need your help and advice. I see this as my only option to own a Rolex, Omega etc. If this is to be my only watch of that level, would it be silly to go vintage? Should I leave that to collectors who can afford models old and new? Is it going to be too delicate or temperamental to rely on everyday for years to come (like a vintage car)? Will service costs be prohibitive?
In short, am I better off sticking to a new or lightly used model in a more realistic price point for my means?

Tell me your thoughts...

Cheers, Mat.