There are tons of places for oil to leak on the driver's side... valve covers, the oil filter base, the tappet cover, the oil cooler, etc. But, if the oil seepage is coming from between the heads and engine deck, then yes, it's most likely passing by the head gaskets. This is often called "wetting the block". Multifuels are known for doing this, lotsa folks drive deuces that are doing this, some even with brand-new, new-style head gaskets, and it's not necessarily a problem unless you're getting oil in the coolant, coolant in the oil, or it's blowing compression to the atmosphere. Many people will not change head gaskets for merely wetting the block, so, it's up to you what you want to do.
As far as the oil consumption goes, 2 quarts doesn't seem like much, but more info than "8 months" would help... how many miles in that 8 mos? 300? 3,000?
As far as the smoke goes... first, do all the "tune-up" things you can do for the deuce... i.e. clean air and fuel filters, make sure your fuel is clean and you've got good delivery via the in-tank pump, and booster pumps, take the hose loose from the front of the turbo and make sure the compressor wheel doesn't have excessive side-to-side or front-to-back play, if you don't have an injector pop-tester, get one and make sure the injectors aren't leaking and are popping within the prescribed range, make sure the valves are all adjusted properly, put it under some extended load driving up long hills to help ensure the rings are seating well against the cylinder walls. Some or all of these things may or may not help with the smoke. If not, you've done about all you can without some level of tear-down... they smoke... when cold they don't have decent thermal/combustion efficiency, so they tend to give some "raw" smoke. When they're warm... they tend to smoke... just 'cause they're 50+ year-old technology.