OPINIONS ON POTENTIAL PURCHASE

I am sure you are already aware that the 3313 movement has had a chequered and difficult upbringing but if that one has been serviced by a OSC then hopefully you shouldn't have any issues. I am not a huge fan of the 44mm Co-ax models as they seem to cram the sub-dials near the centre of the dial due to the fact that the 3313 movement can actually fit a 37mm case and looks more natural in the 42mm variants. That aside, I love my 3313 Speedmaster and much prefer it to the 1861 Speedy Pro which gets very little wrist time due to the issue you mention above and the fact that it is manual wind which is just annoying. I don't buy into the whole Space halo nonsense so have no issue at all preferring the more modern 3313 models. Here is a pic of my 42mm Broad Arrow '57 3313 co-ax model next to a friend's 44mm Co-ax like you are considering for comparison:

Well I am in the UK so am not sure my knowledge or opinions will transfer over the Atlantic, assuming that is where you reside but I wouldn't really want to give much more than $3K USD for any second hand modern Speedy, Pro or Co-ax so IMO that one on WUS is a little punchy on price. I guess the service/warranty is worth a few hundred $ but even so I would want to see it at much nearer $3500 before I would be tempted to put my hand in my pocket. As I say this is just the opinion of an Englishman who likes a bargain so of course YMMV.

Hopefully some others who live nearer you will be along soon to offer an alternative option.

Doesn't hurt to have the leather option. Mine came on the bracelet but I like the look on leather so I use both. If the strap and deployment are genuine Omega then $200 is fair since they are pricey if bought on their own. Make him an offer you are comfortable with and take it from there.