where does it cost you 800 to get to medellin from, Anchorage? You should be able to get direct flights from JFK in the mid 5 range, or connect in Miami on AA for a bit more. I've also messed around with Orbitz and found flights with layovers in CR that get you there, best of both worlds... for even cheaper.
Either way, you should go to Medellin. You are safer in Poblado, stay at a place like the Castillo where you have American friendly ownership and I read (but cannot confirm first hand) that you can bring a girl there and it's plenty discreet. You will still be able to sneak away with the guys to Fase Dos or something so you don't totally miss out on MDE.
You'd be crazy not to go there. Meet her in the Oviedo mall, you can walk there from the Castillo, it must be one of the more "neutral ground" places in South America. Go to eat with her at Parque Lleras. Have the Castillo staff call you a cab, it's a five minute ride, maybe.
Aside from that... let's say you bring her to CR and...
She's a dud
She's not like her pics
You are stuck in the gulch, you at least want to get out to the beach.. now you are stuck entertaining her... and 24/7
She walks by the Hotel of the King and tells you she once worked there...
I have a better Idea, why don't you fly her to Brazil and bring her to a place called Centaurus, I hear it's a really nice place, decent food
I would go to MDE, that way you don't have to be with her 24/7 and if you follow the rules, no issues on security if you do that. And.... you can play when she's not looking.
When are you going to Brazil man? I'm waiting for that report...