I did a brake pad replacement and a clean up of my callipers a couple of months ago there may be anything there that may help you Harley Davidson Community
I have not yet done a write up on the bleeding yet but that may be done soon as it has been a couple of years since i last did the front brake on my softail
if you get the calliper piston all cleaned up and everything in the calliper moving nicely it is wort bleeding the brake
the best method to use is the manual way compress the brake leaver open the bleeder close the bleeder and release the leaver it is a possible 1 man job just need to be in the correct position to get the leaver with 1 hand and have the other on the wrench on the bleeder
just keep doing that till no more bubbles come out of the bleeder so use see through hose on the bleeder
once completed and you stand up straight again you are allowed to groan
I was never happy with the stopping power of my 98 RG. Switched over to lyndall pads, and did the caliper maintenance tips referred to here...major difference.