I'm not aware of any blackout date benefits for lower level elite 1 or elite members. It's only platinum members who can overcome capacity controls.
I would think that if you can demonstrate that you have several million miles on various other carriers that TWA could be enticed to give you Platinum membership. In a business letter be sure to "explain" that your travel pattern will add more Caribbean destinations
http://www.flyertalk.com/forum/wink.gif and they'll review your letter with some inclination to approve.
It's a long shot, but it's better than letting the certs expire.
I'm sorry to hear about your inability to use your certificates. Although I don't understand all of the angst about the FFB Equity award chart (for example, some awards are for travel on Piedmont Airlines), if I had the certs I would want to use them. It is for certain that the FFB Equity Chart has been a big problem for TWA in the recent years for a number of fliers like yourself.
In regards to Avaitor awards, although I haven't asked for award travel to Hawaii or Europe, I have reserved as many as 6 to 8 award seats on a single aircraft for MCO, LAS, LGA, SAN, SJU, and others. The travel plans were flexible and we have had success whenever we needed to receive an award.
If this is a help, I understand that TWA is offering new service from STL to Maui beginning in March. Since that is a new flight, perhaps it won't be clogged with fliers trying to redeem their FFB miles. They announced the flight back in Nov-Dec, so it's not necessarily new news (so again here we might be too late).
I guess one more thing to consider is to use some award miles for Adam Mark hotel nights... 20,000 miles will provide a two night stay.
Good luck, Bil_Flyer. Although I don't see many options for you, maybe it's time for letter on a law firm's letterhead?.