Chip, Maybe I can help you diagnose where the problem is, because I have done this a time or ten in the past.
The first thing I would check is, if you have a vacuum booster above your fuel pump. If you do this could easily be the source of your problem. It is easy to check. Just disconnect the accessory vacuum line at the manifold and plug the opening at the manifold. Road test it a few miles and if the smoking stops then replace the fuel pump. It could be something as simple as a broken or porous diaphragm in the vacuum booster on the fuel pump. (You may need to road test for four or five miles to get rid of the old oil in the cylinders.
There is always the possibility of oil leaking into a cylinder(s) past the head gasket.
To check if it is coming in thru the valve guides is a little bit tricker but it can be done. What you need to do is cut off, or restrict the flow of oil to the lifters, (Yes, your engine can run for at least an hour without the oil going to the lifters)(Just remember to hook it all back up correctly after the test), If you have the "external oil line, as it seems many Stovebolts end up with, then this is simple. but if your oiling is thru and around the head bolt you need to figure out which bolt it is and change it out for one of the others (this won't completely shut of the oil but will restrict it enough to see if the smoking slows down when you test run it.
Another thought that comes to mind is- Don't Chrome Moly rings take longer to "break in" and during this time they will burn a bit of oil? (I could be wrong on this, so I would best refer it ot someone like Jerry.)
Shane,
What you appear to be doing is not rebuilding an engine but reconditioning it. A rebuild would include checking all clearances and having the head, block,pistons, rods, etc. reconditioned or new. Nothing wrong in reconditioning an engine, as long as you know and realize the pit-falls to look for. (which there are many.) If you can see wear marks on the rings, pistons or cylinders, you could have problems. If you don't scuff up the cylinders with a good honing the rings will probably never seat in correctly. If in doubt take your engine to a reputable machinist and have him check it out completely (might be the best money you ever spent).
As to the break in of a "new or new-rebuilt" engine, Set the timing etc. as close as possible. Start the engine and let it get to operating temp., about 10-20 minutes depending on your cooling system. During this time, run the engine at about a 25 mph (around 2,000-2,500 rpm) fast idle. Look for leaks, check the radiator, etc..(The reason for this warm up period is to assure adequate initial lubrication for cam, lifters, rockers, piston rings, pistons and cylinders. In other words, to allow the entire engine to become well lubricated.) Then take it on the road to break it in right- get it up to 30 MPH and accelerate to about 50 MPH, then let off the throttle and let it get back down to 30 MPH. Do this at least ten times. Take it back home and you're set to go, just avoid any sustained high speed driving for the first 100 miles. After that, drive it like you will always drive it and it will respond accordingly.
