I'm a big fan of Trumpet Dan but i went ahead and joined Grapplers Guide. Trumpet Dan is an excellent teacher and his YT vids on Roger Gracie was instrumental to my development when i started, id assume that his site is also as good as that.
What I liked about Jason's is the fact that I can now pick and choose which techs/concepts to add as im now in the process of building a "game". The Grapplers Guide has different programs to suit grapplers of all levels (Combinations, Escapes, Subs, Fundamentals, etc). I especially like his Transitions Program, it is valuable to me since my teacher doesn't teach it too much. His site will probably keep me busy for years to come.
You can't go wrong with any of them imo. TrumpetDan, Jason and Kesting are my go to guides for BJJ on the net and I think they're all great.