After doing some more research on some of my issues, I realized I have overlooked a huge factor in reloading; PSI in the case. As I have mentioned before, I am relatively new to reloading (4 years) and still have a lot to learn. I feel so stupid. Understanding that a 150 grain bullet with 64,000 PSI is going to shoot much slower than a 130 grain bullet with 64,000 PSI, I feel juvenile. I was trying to force the bullet out faster expecting nothing to happen? come on Ryan!!!!

Not sure how or why I wasn't smart enough to think about this, but now that I'm aware of it, some of my issues make a heck of a lot of sense.
Here I was trying to get my 150 gr bullet to fly 3100-3200 fps, I have found very few loads that will allow that with a 150gr bullet. After talking with a gunsmith, it also greatly depends on the manufacturing of the rifle. Remember, this is an off the shelf Winchester Model 70, not a custom rifle so manufacturing of these rifles vary greatly depending on the batch they came from. If the rifle chamber is "tight" it will allow for very little "over expansion" in the chamber, causing cracked cases if you exceed the max PSI for a certain load.
I have learned that the chamber in my rifle is "tight" which is good, part of the reason my rifle shoots the way it does, but does not allow for much vairance when it comes to max loads. That beings said, my rifle shooting .44" at 100 yards with a speed of 2800 fps, seems reasonable with a 150 gr bullet now. Knowing that I can't get much higher becasue of pressure issues.
To confirm this, I just got some 130 gr SSTs that I will load for my brothers .270 WIN. I'm going to try several loads just under max (around the 64,000 PSI range) and see how much faster the rounds will be. I'm expecting they will be around 3100-3200, without over pressure issues. I've never shot 130s through this rifle, so it will be interesting to see what happens. I can't imagine that they shoot as well as the .44" that the 150's provided, but I will keep you posted.
Pretty cool to learn these things as I go along. Hope this is helping someone avoid the same problems I have encountered.