Way I look at it, its kind of throwing the baby out with the bath water for a few dollar fix (if not stepping up to a three phase 50 amp no shunting unit).
Hence old voltage regulator and startor are still fine, its the connector bullet connectors the problems, and since the new one is just like the old one, really not solving the problem in itself in the long run.

So with stator pulled, can pull the female connectors out of that rubber section to solder in new ones with some silicone grease to seal them back in place, and same with the regulator connectoor as well.
You want to use some black silicone on the stator rubber piece outside and channel when you push it back through the case and tighten it set screw so you don't get engine oil leak past it, and with the male connector plugs pulled forward from their rubber piece and a little grease electrical grease on the metal parts, can seat them a hell of lot deeper into the female bullet connectors than the factory plug, then do the black silicone trick on the regulator side wires wires to seal off/glue the male connectors to there seated rubber connector.

Myself, since I always saw the connector with bullet connector at the case a problem, would just re-solder in longer wires off the regulator so they extended out of the case rubber piece, and relocate the connectors farther up line isntead.

Hence on my 97RK, don't have that vibration problem at the motor for the bullet connectors to cause problems, since the connectors for the two are in a small plastic box on the front of the frame isntead.

https://partsfinder.onlinemicrofiche...GE%20REGULATOR

 

This style retainer works great, captures rubber connector snug.

 

I clean off the regulator boot and the stator post thoroughly with CRC 05103 QD Electronic Cleaner and put a bead of black RTV Sealant around the stator end. Then push the boot from the regulator end on and let it cure over night. It seals nicely and everything stays put.

 

I did this also and never regretted it since. Got tired of replacing stators because of the rubber plug leaking.

Also got tired of worrying about that lousy connection point.

 

Well. The Harley gods are helping me out so far. I was able to pull the compensator sprocket without having to pull the clutch. I am going to do like ya'll say seal it off good with sealant. I might even use the retainer that Schex showed. A touch of chrome never hurt either. Should last another 26 years. That means I will still riding it when I am 93 years old.

 

FYI, would still pull the old startor and repair it for back up use!

Never now when the battery in the bike may ***** the bed to cause you to burn up a new stator or regulator, and having a back up parks in play, means bike can be fixed in a few hours; without having to wait for parts. Worst case, problem never happens to you again, but friend of your does cook a regulator or stator by trying to run a dying battery too many years in the bike, and can give them your rebuilds to save them a lot of money isntead.

Hence my run of thumb since I can get a New Die Hard AGM batteries from Sam's for around a C note, come the three year mark every spring, the bikes 3 year old batteries are replaced with a new one like clock work before they start to have problems and take out the more expensive charging system parts instead.
Note, on the old lead cells, cold winters with the bikes in storage off the tenders would do them in even faster, so would replace them every two years isntead.

 

Sometimes it's the littlest things that make the biggest difference.