I think that Air Antilles plans PTP ANU EIS service as an AF code share.
Air Antilles Express needs to expand service to STX/STT.
Interesting topic. Number of issues which you can confirm or disagree with.
1. The bulk of the OECS migration into the USVI was in the 60s and the 70s. This is evidenced by the fact that the USVI population increased from just under 40k in 1960 to over 100k by 1980. Since then the population hasn't increased that much. This is due to massive movement to the USA which has offset more recent migration from the DR and the little migration which might still exist from the OECS.
2. A large % of the offspring of these migrants, and even many of the migrants themselves have moved to the mainland. Many of the older migrants have returned home. STT/STX aren't viewed as favorably as they were in the 60s and many of these OECS islands have progressed significantly since then, enticing some to return home.
3. The 2010 census showed SKB/NEV account for 6% of the USVI population, DOM for 5%, and ANU and DR for 4% each with SLU accounting for 3%. The STX economy has been weak for a long time so I suspect that there are fewer newer OECS immigrants there than in STT, which has a more buoyant economy. This will mean that a higher % of the OECS nationals living in STT will have ties to their homelands than is the case for STX. LI has been dropping service to STX for a while now, even more than it did to STT, that is before the sharp cut of about 2 years ago when STT was slashed from 2X/D to 4x/W.
I say this to say that the OECS population in the USVI has aged and isn't as connected to their homelands as they once were. This has clearly impacted LIAT. I remember in the 90s LI ran 4X daily out of STT and 2x daily out of STX during busy periods. The level of travel has declined even faster than the OECS populations in the USVI has. I don't know whether these islands can sustain 50 seat planes any more, though clearly there must be demand for something better than a 9 seat plane.
I think that the best opportunity for the USVI lies with Winair with its 19 seat planes. I think that STT can support at least a daily flight and STX maybe 5x to SXM. From there Winair can feed into their routes to ANU SKB/NEV, and DOM. Winair and Air Antilles work closely together so there is scope for service to points further south. In fact Winair did fly to STT in times past. Not sure if they ever did STX.
Air Antilles also runs its PTP DOM SXM flight onto SJU, this I suspect being especially for DOM. Don't think they are going to drop that for a less lucrative USVI though I can imagine a seamless connection via SXM..
Another idea might be Inter Carib (which appears to be building a hub in EIS) running EIS STT SKB and EIS STT ANU flights. Maybe an EIS STX SLU flight as well.