Newb questions on breakin (confused)...

How should you feel for "pinch" when rolling a motor over by hand? with the plug in or out?
How do you know when you have lost too much pinch or damaged the motor?

I have the 3port GO sport. I've tried to follow Brian's(Pro Twister) post on break in and I'm worried that somehow I have lost alot of "pinch" after 7 tanks.
I feel no pinch with the plug out after a few tanks, with the plug in I can feel a good bit of compression, but I can roll it over "the hump" with a firm finger...is this normal?

I'll review my breakin so far...

First tank, HSN out flush, LSN 1 1/4 in from flush, preheated (with my heat gun only got to 180), started easy, idled the motor with foil on the head at a nice 230, cooled to 114 at BDC.

Second tank, same ritual but the temp was slightly lower 200, with little throttle inputs I could maintain about 220

tanks 3 - 7 I've been driving it around a little, leaning the HSN an hour per tank. HSN is still rich, temps are much lower even with the foil. I've given up on trying to maintain 200+ temps on the motor because I'm too nervous to lean it out that much. Temps are between 150-180 everytime I check it.

My brother just bought a 3prt race spec and after 5 tanks has a ton of pinch, with the plug in there is no chance on rolling it over with your hand?
He has been breaking his in by running the LSN flush and the HSN out a turn from where it was out of the box, no foil, low heats...

Sorry for long post, I'm concerned about my break in... any thoughts would be appreciated.