My '83 Roadster really likes 60w oil. Unfortunately the oil doesn't stay in it for too long. It's now going through a quart about every 700 miles. It only leaves a drip or two when parked so I'm sure most of it is going out the exhaust.
I'm gonna look at everything from a basic top end rebuild kit to stroker kits. Question is, where to buy an affordable kit from? Then I need to make up my mind whether I want my bike down in the middle of summer or am I gonna keep fogging for mosquitos until fall and then fix it over the winter.
Also I see lots of stuff for Shovelheads but hardly anything specifically for Ironheads. It almost seems like no one except Ironhead owners even know that Harley made an Ironhead.

 

I would wait for fall/winter to rebulid the engine. You will not know what parts you will need until you get it apart and have a look. You will need a top end gasket set, and may need any of pistons, rings, valves, valve springs, valve guides.

With the top end off you will have the opportunity to test for sprocket shaft bearing wear and check the rods for side/updown shake as appropriate - see the factory manual for details.

You will need a good, trustworthy machine shop to check the cylinders for needed rebore, and to do that work, and also to check and fix as needed the cylinder heads. You may wish to send parts to a highly recommended machine shop that has experience with ironheads.

Virtually all automotive machine shops will do the work. All will convince you as you talk to them that they are experts. And most likely they are. But beware of any shop that talks big and has not done work on an ironhead engine before.

If you do not yet have both a factory service manual and a factory parts catalog get both, and spend many hours studying them before you begin this project.