New purchase question

[kiwiAaron]

Hi,

Looking to purchase my first Rolex.

I have a budget to $2500USD which puts me at entry level and used obviously (note: I have three kids, work for a church, live in an expensive city and it's taken me a while already to squirrel away that much on a gratuitous purchase - so increasing my budget isn't an option).

On eBay and C24 there are watches at the price point. Almost all are Oyster, Oysterdate and a few Air kings - which is fine, I love those watches. I've read posts on what to look for in a vintage watch etc i.e. the importance of 'buying the seller' etc.

My question is this - what would do faced with the choice between these two options
1. An okay looking Oysterdate/Air-King with original bracelet
2. OR... An Oysterdate/Air-King with a better looking dial (condition and/or color) but no original bracelet (so perhaps a third part leather one)

Assuming both watches are mechanically sound.

Is there any conventional wisdom around this?