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If the game is telling you its been 2500+ days since they were last at a location, it does sound like your save game is bugged. I have heard of issues like this happening, but never actually seen it for myself. Sadly, only solution is to start over. AFAIK, its a rare bug, not a persistent one.
This depends on what boat you have, or more accurately, what the slowest boat in your fleet is. If you are running around in a sloop or a war canoe with nothing else in your fleet, you will go faster than them.
2500+ days is a bunch of years, by that time he could be literally everywhere in the Spanish Main - NPCs travel just as you do, with the same speed and distances. Just go to the port where he was last seen and talk with everyone. Your best bet is to dance with governors' daughters (they should be at least attractive), if you do well they will give you an updated tip on Raymondo's whereabouts.
I am either the most unlucky person or this game is just completely broken for me. First time ever playing and I cant even complete the game because of this. Put 9 hrs into a save and was doing really well until "baron Raymundo has set sail from Santiago 1255 days ago and is on his way to st. Augustine".
Looked up the bug and found this page, it sucks but I learn I will have to restart. I think, "okay, I can get to this point faster than 9hrs in a new save." I start a new game, get information on Raymundo, he is down at Rio de la Hacha. Cool, head down there asap in my sloop, hes not there (I figured). lets find out where Raymundo is heading now! Oh the bartender says he just set sail from Santiago and is heading for St. Augustine! Oh wow! "I dont like this", I think to myself. Sail up northeast to St.Augustine as fast as possible, what do you know!? Raymundo is nowhere to be seen. I sail around for about 5 minutes looking for information. Every. Single. Place. Again. "Baron Raymundo has set sail from Santiago and is on his way to st. Augustine"
Knowing I am probably bugged. AGAIN. I decide to divide the plunder hoping it resets him. Nope. Same damn bug.
TL/DR
Encountered this bug "baron Raymundo has set sail from Santiago ___ days ago and is on his way to st. Augustine". Started new save, and withing one town of looking for Raymundo I get the same exact bug.
Is it worth starting a 3rd save, granted I didnt get anywhere in the 2nd save? I have a feeling this bug will persist as it happened as soon as I start a new save after encountering it on my original save.
Is there any possible fix? I just installed the game two days ago, and I have installed a few HD texture mods, but that shouldnt affect any gameplay.
I figured it was not the case in your situations, but hey, it did happend.