I can help answer here.
The main problem is the players - internal logic suggests why move if its not worth my while? Your best domestic montserrat players wouldn't play for Vanorama North or South, as they will be below standard. For players to move abroad they often require a premium, which no club would pay for in England. Foreign clubs won't be interested for a long time - you'd need to significantly improve the youth coaching.
My files solve this by setting up transfer preferences, and I have seen montserrat players head to local islands using my data files, as a step to Europe.
Without my Caribbean Shield competition you will find it nigh-on impossible due to the random nature of qualification for you - if you load my files and make it to the group stages you can get good (realistic) cash - about what you are earning a year in revenue!