@motorbreathThanks for your reply. I'm not sure at all if I got all the air out. I think most people would've considered the power steering find, but I'm proactive and doin't like to wait until something breaks to fix it. So as soon as I heard the whine coming from the steering, I began researching. I initially read up about the o-ring, but didn't find out about replacing the hose and clamp as well until later. But I never had a car this difficult to bleed, so I was reaching out to other subaru heads for advice.
When I first changed the o-ring, I wasn't confident in how the fitting was tightened. So I backed it out and sure enough, I damaged the o_ring. I went and bought 2 more at the local dealer. I was a lot more confident in the second install, as the fitting clicked right in place. Also, the system holds vacuum fine.
I am beginning to suspect the old hose and clamp, as mine is rock hard with absolutely no give. (it looks brand new, however) It even still has the yellow marker on top from the factory.
I have the hose and clamp on order, and I'm not driving it until I'm sure all the air is out. I just hope I didn't damage anything in my efforts to bleed the system.
FYI
I initially read to place the system under vacuum, start the car and turn the wheels lock to lock. Then I found an article from SUBARU that says to NEVER run the power steering under vacuum as you can damage the seals. It Also says to NEVER start the car until all the air is out, because it will foam the fluid and make it impossible to bleed it.