I grew up in Cuba so many people ask me about traveling in Cuba. I am hoping this page is going to be useful.
This web site http://www.cubarenta.com is a useful starting point to get accommodation outside the government ran hotels. I found that the lonely planet book on Cuba is very good, also the website http://www.lonelyplanet.com/cuba has good tips.
In terms of when to go. Avoid July and August, it is very hot in Cuba at that time. My favorite times are September - December and April - May.
I also have a few favorite Cuban blogs: http://www.desdecuba.com/generaciony , http://generacionasere.blogspot.com/
I few YouTube channels: http://www.youtube.com/user/cubarenta (houses for rent in Cuba), http://www.youtube.com/user/TrovaCubanaDel21 (Cuban Music).