alright guys so here is an update. Draft at the door of the boiler is .01 (if i'm lucky). At the breech it's .03 (rounding up). So, my next move was to determine if there was any blockage on the chimney. I climbed the roof and dropped a brick down (I know probably not the smartest move) but it did the trick. Brick went all the way through. As my friend/hvac man is looking for brick he notices something. The flu is slightly pulling away from the building. Now don't get me wrong, this flu is still plenty sturdy and strong, just has a crack between where the flu pipe exits the house and where it attaches into the terracota piping to go up the chimney. Which is where we think the problem lies.
Our thoughts are that between the stainless steel leaving the house and where it meets the terracota pipe (which is roughly 9 inches) there is a big crack where air is entering into the pipework/chimney. This is what we believe is causing the low draft problem.
The inside dimensions of the terracota is 7.5 inches which means that it should easily heat up and with it being surrounded by brick it shouldn't be a problem of low temperature or draft issues. The only possible problem would be this crack.
You could slip an SS liner in the chimney and sleep well again. I don't like the idea of air entering someplace in the middle of the run. If you can seal it 100%, that would be acceptable, but still makes me nervous.
When you say "crack", do you mean that something is broken or that there is a gap between the pipe and the thimble? If it is just a gap between the thimble and the pipe, reinstall the pipe with some furnace cement to seal things up.