As you noted, they(Village Fine Wine & Cigar Shop/Magnolia Wine Bar & Bistro, and Bass Pro Shops/Islamorada)are two separate facilities with a connecting passageway. That keeps them in line with the ABC regs on where the boundaries are for consumption on premises.
You are also correct that once you cross the line between one and the other you need to change from CC to OC.
From past posts re: Wegman's in NOVA (grocery store that has a wine bar area) it pays to keep your eyes open for these new combinations. IIRC the wine bar area in Wegman's is not clearly marked off from the rest of the store, but I'll wager that if you drifted too far "out of bounds" someone would come after you to return you to the corral. The problem for those that choose to CC is that they may not be aware of crossing into the corral until it is too late.
I think there are some sports bars in the West End that have "game rooms" that are separate from the club area, but I can't recall which ones. Best bet is to look for teens/youth playing there - they can do that because they are not in the ABC-licensed area.