"What were the odds I was there on his 5 year anniversary of his death?"
I'd say about 365 to 1 were the odds, but some things, and this qualifies as one of those things, certainly can defy logical explanation.
I like your read on these aptly named "checkpoints" you have come across. Good on you to be aware enough to recognize these situations. I like to think that when similar situations occur in my life, that somehow, and I dont know just what that somehow is, that somehow I was connected on some level with whomever it was that the "checkpoint" situation related to, as in their life spirit was in the room. Kinda heavy shit, but I am diggin where you're shoveling from......I enjoyed your "lengthy" sharing of info..
Enjoy the Baja and all the craziness that goes into making your endeavor happen. Sounds like you have things sorted and in the proper prespective. Bad shit that happens along the way builds us into what we are. Looks like your build is right on track!!