Interesting thread....other than Chawk, you seem to be giving yourself most of the answers.\
Personally, when I put a transom saver on for a customer, I just bring the motor down and just barely touch the transom saver. I have see a couple come in where the customer brought the motor down so tight, that the transom saver made a hole on both sides of the lower unit.
I am not an expert on trim units (do not see much trouble with them on Hondas), but here are a couple of thoughts...
You may still have some air in the system. Your bleeding method sounds right, but you did not say when you lowered the motor, that you let it sit for 10 minutes or so and when you raised it all the way up, you took off the fill cap, added fluid, then let it sit for another 10 minutes or so. It there is air in the system, raising it up and down will cause very small bubbles to be suspended in the trim fluid. It takes a while for them to work themselves out. You will have to do this several times.
I just bled a 225 over a two hour period. I let it sit for a long time in between raising and lowering, while I was doing other things. It had a lot of gurgle in it when it came in, but most of it is gone now.
Anyway...
Do you see any other leakage, especially on the tilt cylinder?
Have you ever changed the seals on the tilt cylinder?
When you changed the seals, are you sure you oriented them correctly?
Does the motor raise up when you give it full power in reverse or does the trim hold it in place? If it raises, it could be air or it could be the one or more of the bypass valves (little ball bearings) in the end of the tilt rod are stuck open. None of the parts breakdowns that I know of show these guys. They open up when there is too much pressure like when you tighten it down to the transom saver or if you hit something in the water.
I would first give it another try at bleeding.
Mike