Payton, I had the same problem when I bought my boat last year. I removed both end fittings so I could get a better view through the boom. If the outhaul line is too slack, over time with all the boom movement and boat bouncing around the pulley with the swivel on it turns on itself & binds the line. I also had to drop the forward internal pulley to be able to pull out the blocks & line to straighten everything out and I now keep a slight tension on the outhaul to help alleviate this problem. I also have an internal reef line and having both ends off I could see that the reef line had been run through the outhaul lines so I reran that also. Fortunately I had added a fixed vang so the it supported the boom while it was detached from the mast. I also used a large screwdriver and a hammer and slowly separated the fittings from the boom.
Ron
Ron