I usually ALWAYS buy used (once I bought a new gray market Sub), but last year I wanted the Railmaster LE so badly and couldn't wait, so I bought it through my local OB. Of course I got treated like a VIP, but also, I established very good rapport with a couple of the sales team and we've become friends.
They invite me in to try on some of the new pieces (like the new Railmaster non-LE and the Seamaster 300) while I am treated to a glass of beer or a flute of champagne while we chat watches. It's a great experience and they make me very comfortable (at first didn't think I would be a fan of the "boutique" experience), but it's nice and I want to support the brand directly.
I would suggest you visit your local OB or AD and see if you bond with anyone. That's exactly what I did. I instantly gelled with one of the team members right away (Jake Ross at the Bellevue location) and promised that if Omega does in fact release a retro-inspired Railmaster reissue, that I would buy it new with Jake and that's exactly what happened and I have zero regrets.
Best of luck and keep us updated.