Stubborn cylinder #2 - Can't figure it out!

I have read and have done so on small engines (lawn mower, rototiller etc) made use of rope feed into the spark plug hole to hold the valves closed, but the proper way is to remove the head and make use of a clamp to hold it closed. 

There was no mention of smoke
Does it do it constantly or just initial start up?

Also are you the original owner
And did this just start with the cooler cylinder ?

Now that it's "running" I'm getting smoke during idle and some throttle as well. It's only coming from the left exhaust and it's cylinder #2 so it's my assumption it's the cause as well of the smoke and oil dripping from that exhaust drain.

Not the original owner.

Do a compression test on cylinder 2. Note the reading. 

Add a small amount of oil in the spark plug holes (teaspoon or so). Do another compression test. 

If your compression increases, you need at least a hone and new rings. If it doesn't change, valve seals, possibly guides.