For a while now, I have been getting a lot more red bruising on my middle and ring finger. Awhile back, my hand was getting a bunch of pain in it and determined my span in my middle finger was too long...at least an 1/8 if not more. I can't remember how far I had it dropped but now my span in my ring and middle finger are about the same in span. I did this on a ball I had plugged and redone.

Well a driller I had one new ball do after the span made the finger holes bigger then I cared for and my fingers could go to the first joint. Before, I never put them that far in the ball nor could with the larger span. Then another ball followed and another. Then my fingers, especially my ring finger had bruising on both sides with mild pain. My finger was actually reshaping itself because I was placing my fingers farther in.

A few months ago or less things got worse. The mild pain in my ring turned to ligament pain or damage. At least that is what I think it is but I don't know. Some days after bowling it was hard to even bend it.

Decided on on of my leagues since my fingers in a poor morning practice were already hurting I tried just putting the tips of my fingers in the ball which I haven't tried with my new span and tried it during league and threw the ball terrific and shot over 700 which in that league I have been struggling in. I know must will say your supposed to put the fingers in all the way but I tried that and got nothing put pain. I have also previously tried reverse in my fingers and was just dropping the ball every shot.

I didn't have the problem you had (mis-sized holes), but one of the reasons I stopped using inserts was because I was between two sizes and used to oscillate between the two closest ones.  

Even after discovering Vice brand half-sizes, I still couldn't settle on one size and stick to it.  Since I switched to no-inserts, each ball (at least at the fingers) felt identical.   Had other issues, but at least without the inserts, I can't constantly adjust them back and forth in my OCD (Obsessive Compulsive Disorder) way.   No... I have not been diagnosed with it, but anyone observing the constant tweaking/adjusting I do with bowling equipment, would surely label me as such.

And surprisingly.... my fingers which had started to swell and shrink somewhat, have never done that since switching to no-inserts. Not sure why, but added benefit has been consistent feel in the fingers.  Only the thumb size has been a continuing problem in the 2 years since I stopped using inserts.