This seems like another Puerto Rico situation IMO. I don't see it happening.
FWIW, I do think either this needs to happen or it be absorbed back into Maryland. That and getting Puerto Rico to be a state, and other US territories into the Union more properly has been a can kicked down the road for far too long. It's dumb to have "US Citizens" not be able to actually be legally represented in congress. That is literally the issue that caused our own war for Independence.
Knowing some folks down in PR, they're typically polarized on the statehood question. I think their best long term prospects are as a state: their economy is just too closely tied to the US. Their governance is just fubar though; it mostly resembles an old school early 20th century urban political machine. Patronage, protection, and graft. Everyone has a sort of societal Stockholm Syndrome point of view due to the abuses of government.
There is enough ethnic/social pride to make the statehood question pretty divisive for them internally though versus independence. What they really need to succeed is infrastructure and business investment. In the current world economic climate, I don't see anyone stepping up to the plate. Maybe China, but there's not really anything there for their efforts except a thumb in the eye of the US.
Tragic really, its natural beauty and culture is awesome; given some stability, it would could be a real gem. Its worth an extended visit; the interior mountains, the coasts, Old San Juan - all fabulous.
