I think we will get a friendly on June 1st, if not then pretty soon after. If that ends up being the case, I guarantee it will be the usual suspects: St Vincent, Grenada, Guyana or St Kitts.
I understand that it comes down to money in order to play the bigger competition. However, take for instance the JA football federation, they have had much more financial difficulties than TTFF, but for some reason JA continues to generate interest for friendlies. Especially friendlies from true football nations.
As far as I am concerned the TTFF needs to work more on their marketing and communication strategies to gain more interest for good quality international friendlies. I think they do a poor job of promoting and increasing the visibility of T&T football to the rest of the football world. Perhaps they could start by broadcasting all upcoming friendlies on their website and archiving them. Not only the fans from abroad will get to see it, but also other football federations. This will give football federations an opportunity to always refer to something when they are looking for friendlies or deciding whether or not to play T&T.
If I was a foreign coach, I too would be reluctant on scheduling a friendly with T&T. Because, I would not know what kind of team will be coming out to play. If I had to choose between JA and T&T, I could easily find videos on JA last games and make a worthwhile decision. For T&T there is not much recent evidence to convince me to choose T&T over JA.
Trust me its a marketing and communications problem that preventing the interest for good quality friendlies. International teams will continue to go elsewhere for friendlies unless this changes.