If you have the head off lift the jug up as far as possible and block it in place, wind the engine over until the gudgeon is clear of the bottom, pop it out and wind the rod down as far as it will go, push the piston back up into the bore a bit if you need more room, that's what I have done if clearance is tight on customs, don't know if that will help you or not.

Easy as.....   Put a jack under the engine and raise it so its just touching the bottom.  Then basically remove all the front engine mount bits which will result in the engine now resting on the jack.  Simply lower the jack, the engine will lean fwd and you have easy access to the rear jug.  (can be done with the bike upright or on the side stand, but upright works best.)

What they said  just stuff the case with some clean rag around the rod not to much 

Hey fellas going well so far just need to know what size these are?

Head bolt? Think it's 1/2"

So another update pulled the rear cylinder of to do a top end rebuild. And any reason why the middle gasket would be tripled? And the base gasket was non existent, just a big silicone mess in there. Also to get the room for a standard Allen to fix I used a ratchet strap to move the engine around 3cms to get in. Super easy and worked great! 

That's just a stock Harley headgasket man, they usually pull apart when you take the heads off.

Yep... normal head gasket.  Base gaskets are always paper thin (invest in GOOD gaskets like James or Cometic  (and MLS only which if i recall is the bees knees for heads)

Got a James top end rebuild kit waiting at the post office, just curious about getting the piston back onto the barrel. Do I need to get a piston ring compressor? Or is there a sneaky way around it?

The rings are a chit to do without a compressor but can be done if your gentle.  One approach is to mount the piston into the jugs BEFORE you then slide the jugs beck into the bike.  You then do the gudgeon pin etc before you slide the jug into final place.  (WARNING - its bloody easy to drop the c-clip into the cases here...lol)

I've been reading the service manual flat out and just said stuff it and grabbed one from super cheap. The new gaskets look great! Now just need to clean all the silicone mess up as good as I can after work and hopefully get enough time to start putting it back together! Its about now i had a full length video tutorial haha

One thing.  With the jugs out, check both mating surfaces between the jugs and the cases for levelness etc.  I found casting rises and 'unsmooth' bits on the cases that i actually filed smooth (And thats okay to do so long as your using the right file and being careful).  Every little bit helps when it comes to sealing.   

Progress, agree with all the above, just asking here, new rings an a light hone or as she was?

Bugger.  Did you make sure the base gaskets were on correct and not covering the oil return hole?  

Did you check the pushrods aren't mixed up? They're different lengths. I fucked it up the first time I did it. Bike started but ran like a three legged goat.

What Smokey said in regards to push rods  there colour coded for each valve and 

So how did you go?

And just buy adjustable pushrods.  They will save you money when you put in the hot cam etc.