Update!
Well I got me a fender roller and went at it! It has been raining here for a week so that is why the wheels/car looks like crap. Heres what I did...
I removed the wheel well moulding and started out by installing the roller and getting my first round adjustment set. I then used a heat gun on 10-2 o'clock section of the fender. I heated the bottom edge and rear of the lip to avoid damaging the outer paint. Take your time and get plenty of heat in the lip. This was my "beginning" angle on the wheel.
I used gradual adjustments to eventually get a more aggressive angle on the roller to "turn" the lip in.
I made "slits" in the wheel moulding and reapplied to the car. On the first side I used the roller to roll the moulding to match the fender lip. (I later discovered that a rubber mallet works MUCH better and gives a "tighter" fit not to mention the roller DID crack the paint and the mallet DID NOT???) After I rolled the moulding to fit it was removed for the next step.
As you can see in the previous pics even with heating the paint it will still "crack" although I thinnk by heating it you will only see cracking where the roller is making contact in the sharpest portion of the roll. The fix was to sand the underside/inner lip, mask it off, and paint it with black Caliper Paint (seems very durable and adheres well in my experience)
Here is a view of the lip with the moulding applied from underneath the wheel well.
I will post some before and after pics next.