I know this wouldn't have anything to do with your 5th gear pushrod adjustment, but I had a 96 Heritage that 1 day just wouldn't downshift. I did a clutch adjustment, primary chain adjustment, shift pawl adjustment, and the problem went away. Pretty sure the shift pawl was the trick.
3 inexpensive adjustments that can't hurt to do.

 

That is certainly possible. My plan was to adjust the primary and clutch tomorrow anyway because it has been a bitch to get into neutral lately. Ive never heard of adjusting the pawl and cant find a procedure. Can you explain how to do it or post a link for it? I figured I gorilla'd something when I was banging the shift lever by hand while rotating the rear wheel back and forth but, looking at pictures of the internals of the transmission, it looks pretty stout so, I may be OK on the inside. I did check the obvious, shift linkage, etc.. Also, I juts serviced the trans and primary last week. I use HD Formula + in both. Im never sure exactly how much oil to put in the primary and may have over filled it a bit. With the bike level and primary cover removed, the oil is right up to the bottom of the cover opening. I just poured in the amount the manual said to.

 

https://www.hdforums.com/forum/prima...g-problem.html
I'll check to see if I have the procedure.
https://www.hdforums.com/forum/softa...problem-2.html

Procedure for 95-96 ST
Shift trans into 3rd gear - be sure it is fully engaged in 3rd.
Move shifter lever and feel for free play and spring pressure in both directions.
Use pawl adjustment tool H-D 39618 (I bent a wrench to fit) and loosen the locknut. Adjust the allen screw in 1/4" turn or less increments (either clockwise or counterclockwise) until spring pressure and free play is equal on both sides of the shift lever travel.
Recheck adjustment and tighten locknut.

This procedure is right after shift linkage adjustment in my manual.

 

Thanks T ! Your thread describes what mine is doing exactly. Hopefully, I'll get as lucky as you did!

 

That is part of the problem right there.
Harley found that filling to the derby cover opening was causing hard shifts so they changed the required level to just touching the bottom of the clutch hub pressure plate.

Me personally I just throw in a quart and call it good.

Also some people have said that the Formula+ causes clunky shifts.
You might want to change what you put in there.

BTW tranny should have a good sever gear 75 - 140 fluid in it.

 

Well heck..I had no idea. The Formula + bottle says transmission and primary so, thats why I used it. Ive definitely got the primary overfilled. Dr. Hess said he uses ATF in his primary. What are you using in yours THC ? Ive got some Royal Purple 75w-140 gear oil that I could put in the tranny.

 

I have a '96 E-Glide and had trouble shifting, felt stiff and at times did not want to go in gear. Found the spacer plate in the center of the clutch pack went bad. Replacing the clutch and spacer plate fixed the problem. I have used Formula + in the primary since it came out with no problems.

 

I use ATF as well.

I think that Royal Purple would be a better choice for your tranny.

 

I`m going to disagree with that. The five speed gears don`t need any type of super gear lube, they are very lightly loaded and will outlast the bike using any regular 85w90 gear lube.

I have a 1989 gearset on the bench with 115k on it (all it got was 85w90 conventional), and the gears look excellent.

 

i use atf also. derby cover off and the bike leaning on it's kickstand how it normally sits, i'll fill the primary until it's just below the derby cover opening. i have no idea how much goes in there. if you filled with the bike level, you have too much in there.