It's your life, but I'd say why wait? You could use that "wait until I'm good enough" reasoning for the rest of your life.

Here's a couple of other pointers I thought of while Mudcat was down.

Michael Low Chew Tung is a musician from Trinidad who has written a book "Kaiso Koncepts" which should be useful to you. He's also written a book "You can play Calypso Guitar" which I'd recommend to any guitarist who wants to play in a jazz style. His site is here:

http://elan-parle.tripod.com/kaiso_koncepts.htm

He's also posted a number of tutorial videos, here's a couple:

http://www.youtube.com/user/elanparle#p/u/45/RLgBhDgee7o
http://www.youtube.com/user/elanparle#p/u/51/wV7TOB36JC4

Secondly, there is a 10-CD collection "Calypso West Indian Rhythm" Bear Family BCD 16623 JM which collects every calypso recording from 1938-40. This is a fantastic resource for anyone interested in old-time calypso. It comes with a book containing all the lyrics plus many articles that put the songs into context, information about the calypsonians, the origins of the music, the musicians, etc. It's on Amazon:

http://www.amazon.co.uk/Calypso-Indian-Rhythm-VARIOUS-ARTISTS/dp/B000GQML8M/ref=sr_1_1?ie=UTF8&qid=1313656323&sr=8-1

or from the publishers:

http://www.bear-family.de/repertoire/various-bearfamily-1/folkworld/calypso-1938-1940-10-cd-box-316-page-book.html?lang=1

This really is invaluable. It's expensive but I hear you have a birthday coming up!