93Bandit, I doubt anyone can accurately tell you when that the charging system will fail. On the other hand, nobody wants to tell you it won't fail and have that on their conscience if it does happen. You've read enough on this topic to know the risk and can now make a tough decision, but
you have to make it. (Sounds like your seriously considering the R/R swap, but I typed most of this yesterday and figured I'd finish and post it.)
I will say that my charging system seemed fine with 27k miles on an immaculate, near mint looking bike. It lived in the dry desert southwest, in a garage of a mechanic school's instructor. Needs nothing, he said when I bought it (which was far from the truth). New battery, cranks strong etc. etc. After sorting many hidden issues with this new to me bike, I decided to head out on a 400 mile trip which went just fine. Later on, during my second trip, after 500 miles, I found myself stranded in the middle of nowhere. Couldn't bump start, battery was shot, R/R fried! Called my wife from a dying cell phone and waited for five hours to be rescued.
The good side of this story is that in the middle of the Alamo Navajo Reservation, at midnight, with no clouds in the sky, one can see the Milky Way and it leads to deep thoughts about our existence. About how so many people groups exist on this spinning rock and we all speak different languages. Some, being more technologically advanced than others and one group, in particular, on an island in the Pacific was able to engineer, assemble and mass produce millions and millions of these machines that so efficiently carry us to such uninhabited locations. Furthermore, one of these methodically assembled machines transported me to this magical place, waiting until this precise moment to reveal it's secret. Oh, how many millions of people around the world, in utter silence and solitude, must have gazed upon the heavens pondering the answer to this question.
Now, in this moment, this long moment, of pondering why, why did it choose this exact place and time to reveal such a dark secret? You, my friend, have an advantage. You have the opportunity to never need to ask this question.
So, in my case, the R/R failed. I had good grounds and thought I had cleaned and used dieclectric grease on all connections, but maybe I missed one or the unit was just done. When that unit failed it let the stator pump way too much power into the battery putting a strain on the battery and the rest of the wiring. In all, after a wonderful evening under the stars, I ordered an SH775 and purchased a new battery. The stator lasted another 18k miles before giving up. Fortunately I was in town this time and could bump start when I had to shut off the engine.
A volt meter to monitor your charging voltage would help you at least determine if you need to ride to a civilized location before shutting off the bike. If the voltage varies out of the 13v to 14v range you'll know right away.
Just for reference, here's where I was star gazing that night. Took this at dusk. Thankfully that haze on the horizon didn't block the view after dark.