To a degree, its down to the age old measurement of popularity. If the stadiums were attracting 4-5,000 per game, more advertisers would pump money into professional football and press and media coverage would increase.
At the moment, with attendances sometimes as low as 200, local football is a niche sport. Its a chicken and egg scenario. The clubs want to attract supporters, but lack the funds to promote, yet without supporters, sponsors spend their money elsewhere.
We can complain about the clubs, the Pro League, the standard of football etc, but the reality is, we don't go to watch matches. The community argument is valid, but, again, the reality is that across the world people travel 20,30,40,50 miles or more to watch their team, in terrible weather conditions and at a high cost.
Try going to a professional football match for less than the price of two bottles of beer anywhere and you'll struggle. And travel from, say, Arima to Larry Gomes is only $3. So its not cost that's the problem.
And the performances of Caledonia and W.Connection in the CFU prove that the standard isn't bad.
I think the reality is that Trinis just aren't interested in local professional football. What I can't figure out is why that is. After all, back in the day thousands would watch football matches and there's still good attendance at school games.