That sucks, there are a lot of people who make lots of leagues without testing. My Caribbean Megapack has all accurate and tested leagues - Puerto Rico funnily enough only has one level in reality so they didn't get that right either...
If you want a hard, long slog then pick Trinidad or Jamaica. If you want a medium slog, then pick one of the French nations (Guadeloupe, Martinique, French Guiana, Haiti) or Suriname (competitive leagues, reasonably enough to go a distance in the Caribbean Cup). Otherwise you'll find it's easy to dominate domestically but hard to break the NACL (e.g. Guyana with the insane number of regional leagues below the first division, Barbados, Antigua, Curacao, Saint Lucia, Saint Vincent all have 3 leagues to sink your teeth into).
Some of those leagues have interesting rules. Saint Kitts only has two levels, but draconian discipline rules.