[mpipes]

The doctors didn't note any kind of tears anywhere?

The deltoid and the smaller supraspinatus both work to raise the arm in the fashion you described, and both have attachments to the spine on the shoulder blade. If doctors havent found any tears then inflamation could be due to strain caused by tightness and muscle imbalances.

The weakness with hanging leg raises is a separate issue, but as it involves muscles such as the lower trapezius, rhomboids and pectoralis minor, all which attach to the shoulder blade and work to retract, depress and stabilize it, if those muscles can't do their jobs you will feel the affects of it where you have you recurring pain as the shoulder blade will be pushed out of position.

For starters, to work your abs like this without killing your shoulders, do reverse crunches where you lay on your back and attach a pulley cable to your feet. Bend your knees and bring them to your chest. Same movement as the hanging raise without involving shoulders (at 230lbs, I know what you mean about shoulders not liking hanging leg raises) These are killer, I freakin LOVE them.

For the shoulder it's hard to say without getting hands-on or seeing detailed pics for assessment, but it could be as simple as improper bench press technique or posture where you tend to roll the shoulders forward which causes the anterior (front) portion of the deltoid and the pectoralis minor to shorten drastically, which places strain on the posterior (rear) portion of the delt and rhomboids as they get continually stretched. This stretching also causes them to go inactive, where they won't work properly. Some vigorous massage and other soft tissue work to loosen up the whole area would be a good place to start. Then if you can see any signs of muscle imbalances like tight chest/shoulders or arms rolling forward you can work on a training program to balance those issues out.