Hi Marc
To answer your last question first, go all out for a fortnight.
Our first trip was for just one week and we left feeling that we should have stayed longer. A good excuse to go back again though.
There is a surprising amount to see and do and if you want to spend some time, crashed out on a beach, then go for the two weeks. No rush, no hurry, just relax.
You've hit the nail on the head with your praise for this site. Although Steve will doubtless reply in his usual modest fashion, this site contains more info than you will ever need to make your stay complete.
Regarding flights, accomodation, getting around etc. you have a number of choices.
Many people just walk into their travel agent and book a package to one of the hotels. If you are a novice traveller, then this might be the best course of action. Refer to this site and check out the hotels. They are all listed with reviews and comments on this forum, with comments ranging from the superlative to the average. Very few complaints generally though and the standards appear to be generally very high.
If doing your own thing is more your style, then arranging a holiday to Tobago coudn't be easier. You can do it all on-line or over the 'phone.
I booked a forthcoming holiday in a few minutes the other day, Secured the accomodation and then booked the flights. Check out the FAQs the low-dawn on flights with Virgin, BA and Excel. You pays your money and takes your choice but I would recommend Excel via Golden Caribean. Standard fares of around £350 return compared to £500 plus with the others. Also check out
http://www.holidayintobago.com as there is some useful info on flights there.
You can book your accomodation direct, via the links in the accomodation section of this site or you could contact Patrick or Glyn (YES Tourism and Holiday in Tobago - links somewhere on this site I'm sure) who will book accomodation, transport and excursions, give advice and help and assist you in any way that they can. They live and work on the island, so know all the up-to-date info (except what the weather will do) and many myTobago fans have found their services invaluable. They will find you hotels, villas, guest houses, B&B, appartments or private houses to suit your budget.
If you're looking forward to seeing the real Tobago, don't go all inclusive, because you'll be tempted to stay in the hotel to get your monies worth.
If you don't mind self catering then an appartment should a good bet and will allow you to come and go as you please.
If you fancy a break from the cooking etc. then a half or full-board hotel package would suit you sir. This will still give you the freedom to explore (one of the joys of a holiday on Tobago) either with a hire car or guided excursion.
If you have any other questions, just ask away. I'm sure that someone will know the answer, or it will be found in the various topic pages of myTobago.
Welcome to the Tobago fan club.
Cheers
Steve Pitts