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[ltank]

Well, I broke down and ordered the majority of tools to replace the seals. I don't have the part numbers in front of me.
  I ordered Jim's Spocket Lock tool. George's Garage was sold out. I made sure it wasn't the Sportster version. A MBS 1 7/8" transmission nut socket, MBS tools to remove and install the S&S shaft sleeve, MBS Crankshaft seal,George's tools to install the big and small shaft seals. I have a OEM HD Service Manual. Did I forget something? I am very careful not believe everything i see on Utube. Do I need a new transmission sprocket nut? What brand bearings and Seals with part numbers will I need?
 I have 98 Road King, S&S V124 and  Baker 5 speed O.D. gearset. If bearing turn easily without any flat spots or dragging or Noise that's great. If bearings are needed I will go with Baker I guess. I have rebuilt Shovelhead 30 years ago when I was younger.
Recommendations on seals? Almost 40k miles on bike since install of Motor and transmission.
If I find that I need to pull the main drive gear,  I will order a kit from OTC. It's half price of Jim's.
Who makes best seals? Thanks Guys.

[ltank]

Baker 6 speed O.D. gearset. Type error above. I have two weeks to work on it because of Quarantine for two weeks. Possible exposure to COVID.

[TN]

Have you tore it down to verify what is leaking? On the main drive big seal I'd use the baker seal, replace the spacer behind the sprocket too, the main drive bearings should be obvious if bad upon inspection. The OEM sprocket nut is cheap so I'd say yes if going that way.

Just because you're in so deep it's common to replace the other seals too, to be honest my only real world experience is with my 09 and I tend to learn the hard way 
I didn't become a DIY'er cause I wanted to. 

Again it sounds like you have a handle on this project, good luck.