Timeframe Between Jamaica and Back to NY?

Doug says his bar is opening in a couple weeks when they're still in Jamaica and the next scene shows Brian back in New York living with the cougar. Brian visits Jordan who's still not showing a pregnancy pouch and then goes to see Doug in his bar after the breakup with the cougar...Doug's bar seems to be doing well in a short amount of time yet he laments about blowing money.

Exactly how much time was supposed to have passed?

When theres no more room in Hollywood, remakes shall walk the Earth.