Hi Jason
Welcome aboard!
The real High Season hasn't kicked off yet so you should have no problem finding accommodation anywhere on Tobago.
Sadly the local Internet ISP is probably amongst the worst in the world. They 'eat' mail like nobody's business, so don't read too much into the fact that you haven't had replies to your emails.
Speyside sounds a great choice given your interests. Its also the home to the island's best birding guide - Newton George. See our Out & About/Activities/Bird Watching article for contact details, but be sure to contact him once you get there - you will be in for a treat.