Sean:
Some good info here, but let's start with some basics:
What color is the smoke? White or gray/black?? White might mean that your piston rings haven't yet seated. Gray/black usually points at fuel problems.
Does it start hard (lots of cranking) after sitting for a while (1-2 hours or overnight)? That could point at fuel percolation from the bowls so they have no fuel until the fuel pump fills them again (usually 5-10 seconds) before it'll start. This may or may not cause smoke from the exhaust.
Does it start OK when cold but starts hard after running and warm-up and then sitting for 10 minutes when hot? That would point at (1.) either stuck pilot valve(s) allowing excess fuel into the bowls and overflowing into the cylinders and then draining into the oil/crankcase. THAT can be checked by removing the dipstick and smelling it. You should not smell any raw gas on the stick. If you do, stuck pilot valves. Stuck Pilots almost always cause hard starting and a cloud of black smoke.
Or (2.) your fuel hose might be too close to the exhaust causing fuel percolation and a bubble which the mechanical fuel pump cannot overcome. This will cause hard starting but usually no smoke.
Regardless, tell us where you live and maybe someone can help with a trustworthy mechanic/shop or fellow speedster guy in your area. also, fill us in on some specs for your engine: external oil filter? External oil cooler? What kind of carburetors (Kadron/solex, weber, Dellortos or other? ("I don't know" is an OK answer at this stage of ownership).
....guess that'll do for now.
Oh, and BTW: You should be changing your oil at about 300 miles on a new engine, and then I would change it again at about 1,000 miles. After that, every 3,000 miles or 12 months, which ever comes first.
And you'll probably get a lot of differing opinions on proper engine break-in. I would email Roland Rascon, above, as he probably built your 1915 engine, and ask him. Personally, I just drive it as I normally would, just taking it easy for the first 500-600 miles and varying speed up and down if on an interstate.
Welcome to the madness!!
Gordon
The Speedstah Guy from Beaufort