Longtime lurker with a dim distant past of watch collecting, but only recently having gotten back into it. Now, after a good while saving up, searching and being persistent, I've arrived at a steady collection of 3 classic Omegas which I hope will follow me around for years to come: + Watchco Seamaster 300 (cal. 552 on 1171/633 bracelet, ordered direct) + Speedy Pro 3570.50 (on NATO from gasgasbones, bought in person from the affable Kringkily) + 50's 265 cal (on Hirsch leather with Omega buckle, bought from Clydefrog on Watchuseek (great guy, seems to still have more to sell from his clearout)) Seems like I've been quite bitten by the Omega bug, and I'm hoping the fantastic handmade 3-slot watch roll from Erik at http://instagram.com/decamp_goods will limit my buying anything more too soon, though I am looking rather wistfully at Flightmaster 910's... I'm really delighted with the watch roll by the way, if you want one, do email Erik and see what he will do for you - brilliant service and the quality is top notch.
Unless you are wearing a watch you haven't mentioned, I think you have room for at least one, possibly two more - three watch roll or not...