First for the confession-I bought my first home with my wife and have been rebuilding it for the past year and a half, while having a child (wife, not I...) and starting a new job. Therefor, it's been almost a year since my Harley has been ridden.

Life is finally slowing down enough that I'm motivated to get back in the saddle. I knew my '95 Wide Glide was leaking primary fluid, but didn't know how much until last night when I got it up on the table. The primary is bone dry...

I'm looking at gasket kits, and it doesn't seem like the inner primary gasket goes down low enough to cause the primary to leak completely dry, could this be isolated to the main, larger primary gasket, or is it possible to leak all the primary oil out from the inner primary seal?

Also, if I"m going to go ahead and replace all the gaskets, anything else I should replace while I"m in there? Primary bearing, any other wear items?

 

Don't know about leaking that bad, but I have a leaking inner primary seal on my 2010 WG, I pulled it all apart last night and going to dealer to get all the gaskets, seal, bearing and race. Once I got it apart the bearing rolled smooth, looked good except it had some discoloration as if it was running hot. Closer look at the race showed galling and pitting.
Everything is right at $100. So I'm glad I decided to fix the leaky seal.
If your leaking that bad it should be very evident where the leak is. But I would replace everything for PC of mind.

Bad picture but dead center of the race you can see the damage. Oh yes, 45k on the Odometer.

 

If your bike has been unused for that time there are few places the oil could disappear from, assuming there was any in there when you last rode it! They are indeed the main chaincase cover gasket, also the drain plug, possibly the lower cover retaining screws. It is not safe at present IMHO to even consider the shaft seals, until you start riding regularly once more, as they can only leak oil while the bike is moving. So in the meantime change the cover gasket, refit the drain plug with care (it has a tapered thread) and refill with oil as per the book. Having done that you could put an old newspaper under the bike, to provide witness to any drips, especially after you have ridden it again.