First off, I have an '09 SERG with Fullsac 2.5" baffles, Fullsac canned map and TTS Mastertune. This bike runs great. When I swapped out from 2" to 2.5" baffles, I expected a bit of a loss in the lower rpms for torque, but my seat of the pants dyno tells me I'm still good to go and didn't notice anything in performance, just volume of the exhaust.
I agree that lugging is associated with over working at lower rpms. That being said, I often ride in 6th at 55 to 60 mph on level roads without any "lugging" issues. I can speed up at those speeds in 6th, but I do it very slowly with the throttle. If I need to get up to speed faster, I down shift.
BUT... I've just done my Andrews 30 tooth upgrade. Mainly I did this for low gear two up. Both my '08 SERK and my current '09 SERG have had issues, at least in my mind, with starting up from a stop. I have to slip the clutch a lot. Also in parking lot situations in low gear the speed is too fast on idle and I have to work the clutch to stay slow. With my '76 FL 4 speed I can let the clutch out and just idle at walking speed. Sooooo much better in my opinion.
I've only test ridden the bike now for about 5 miles with some on the freeway and some side streets. First gear does seem to be better, but what I've noticed was when doing the high speed freeway entrance run, when I hit second gear it seemed to want to pull the front wheel off the ground. I'm sure that's only in my mind, but it was REALLY a lot better for run up. I also changed out my primary oil to Redline Primary Oil (old label MTL). This may also make some difference as to how the clutch works. But that second gear speed shift was like this bike had never done before.

I'm sure my 6th gear will now be more in line with normal speeds and rpms. I don't run 85 to 90 going down the freeway so at 70 to 75 I'm going to increase my revs by maybe 8% and that's not going to be an issue with me. Or really that same increase in all the gears relative to speed. Some say that with the this sprocket swap that mileage will drop. Based on my riding I don't think I'll see much if any drop in mileage. I typically get 44 to 48 mpg two up. But I do ride conservatively compared to many others here. We're like Sunday drivers on Saturday... We mainly ride alone and just enjoy being out and riding around to nowhere in general, as long as I get my chocolate ice scream at some point in the ride.

I think it's going to be a BIG improvement overall, especially when I'm out in Sturgis area. We're staying in Keystone and 16 from Rapid City to Keystone is long and gets increasingly higher the closer to Keystone. When I had my '76 FL Shovelhead there in '06, if I didn't hit the hills at 65 or above, I would just lose speed until I had to downshift into 3rd gear. Then I was over revving and it was an endless cycle, not good on the motor at all.
A couple years ago I was on a poker run with some other CVO guys and I was running two up and he was single up. My wife and I were riding along in 6th at about 55 and he was having to run in 5th because he said his bike was chugging/lugging/jerking. I guess not all bikes are created equal in that respect. Maybe I have a VERY good canned map for my bike and that's the saving grace to running a bit slower without lugging the bike.
Sorry I digress...
I'm just saying that lugging is subjective. I know what lugging is; I've been a motorhead since I was in grade school. Anything with a motor and I was hooked. So at 55 to 65 on my bike and maintaining speed on level highways I was not lugging. If I was going up a grade or had to get up to a higher speed quickly, then I down shifted to keep from lugging the motor.