Remember cold weather will put you on the lean side, so if you just touch lean then you'll be good when the weather breaks. Pulling the vent will smooth the transition between jets, I don't know why this works I'm sure someone else can elaborate. I went to the S&S site to find the tuning guide and they only have this lame quick guide up.
Here's a wide open throttle test for checking the main jet. It's a simple test and easy to do, I mark my throttle in 1/8" increments with a sharpie for this test. This is actually from the roadstar site but it will work for a BD just fine.
To get best results, we need both load and RPMs. Given that the needed RPMs would equal extremely high speeds in fifth gear, I prefer to do it in 4th.
On the freeway in 4th gear, accelerate at WOT (wide open throttle) to 75 or 80 mph (the higher the better). Acceleration needs to maintain for a couple of seconds to use up the squirt supplied by the accelerator pump. (ignore this, your accel pump should be off!) I like to start around 55 or 60 mph. After getting up to the appropriate speed, back off of the thottle 1/8th turn. While doing so, pay attention to your RATE of acceleration. You will still be speeding up, as you are still in a nearly full throttle position, so rate of acceleration is the key (feeling of acceleration or momentum).
Bike wants to increase rate of accelleration. Main jet is lean and you need to increase main jet size.
Bike wants to maintain accelleration, or feels like you have done nothing different when backing off. Your main is right on the cusp, slightly lean.
Bike looses some momentum (may still be accerating, but at a slower rate). The main is not lean.
This test will not help to identify a rich main, only a lean one.