I don't get on here often, but here's my 2 cents on replacement, since I did end up swapping my hose out a few weeks after my last post with the pics of it leaking.
Do it when you're doing an oil change, and get a deep 14mm allen wrench. After you remove the oil filter, you can stick the 14mm allen inside the threaded stud that the filter would screw onto, and you can unthread it to remove the oil cooler. The coolant lines can stay hooked up to the cooler, you can pull it out of the way to make room. This gives you MUCH easier access to the PS pump for the PS line. Hose replacement was straightforward from there. Just getting the oil cooler adaptor out of the way makes things MUCH easier. Little bit of a cramped area to work, but nothing super tricky about it.
As for bleeding, I had to start the truck a couple times and shut it right off, to purge any air out or it would foam up as it sucked it down to re-fill the new hose. Made a little noise for a few miles, I would just top it off a tiny bit each day until it stopped making noise and was at the fill indication line. Turning lock to lock helped purge things out.