Take the few extra minutes to remove the oil tank and thoroughly clean it, ( or replace it with a late model tank- they are not that expensive) and replace all rubber lines. You don't want some left over piece of pump ruining your new build.

 

The time to do that is definitely when the engine is out. I hang the trans with top mounting holes and a ratchet strap over the frame. (under wire harness)

 

Like the pic above

 

There ain't any way I'm pulling pulling a motor out without a hoist... I put the bike on the side stand and use an engine hoist.. I don't use the strap method but slide a small wood scarp under the tranny at the motor mounts and let it rest on the frame.. No straps to mess with..

 

There's no way I could get one out of the frame without a hoist either. The wood under the tranny across the frame rails is a good idea for sure. The strap helped me on re-install because I could raise and lower the trans to align the dowel pins between the engine and trans and not mess up the gasket in between.

 

R&R presses and welds the crank, did they not do that to yours? Curious, as they just did a new crank for me...

 

I used the strap on install for the same reason

 

I'm sure it was welded.. Welds really done do much other than crack..

 

Before I removed my engine last month the most complex tasks I had undertaken on my Harleys were installing Big Radius exhaust on my Dyna and changing out the handlebars and slip ons on my Road King. I followed the service manual meticulously. I searched YouTube for videos when I wasn't sure about the instruction in the manual. I asked questions here when that failed. It's definitely a doable project for a novice.

I did chicken out when it came time to reinstall the engine. Mostly because I was anxious to ride it this fall before the few remaining days disappeared and I had a lot to do at work. I went with the S&S 124" motor. Loving it so far! It really wasn't much more expensive than a big bore plus the crank work you're contemplating. There are less expensive options though, including installing a take-off low mileage 103".

Good luck and have fun!