At a recent meeting of the Authority, plans to redo the baggage system, replace the air conditioning system, improve the runways and alter the layout of the building were discussed. The cost estimate was about $20 million, according to a report of the meeting by the St. John Source.
The big problem, and the reason you may still miss your flight because the baggage check-in system sucks, is of course, Money. The Port Authority doesn't have it.
The economy has socked the PA's revenues, down about 10% or $4 million for the year. And then there's the fact two VI government agencies, Natural Resources and Water and Power, which lease office space in PA buildings, owe $472,000 in back rent. American Airlines owes a few hundred thousand dollars more.
So … sounds like using carry on bags is going to be the best strategy for a long time.