Others can reply about the engagement issue, but don't waste your time or resources changing the trans fluid. That horse is way out of the barn for a flush to make a difference.
I had an issue with my 08 CSS downshifting from 3 to 2. It would grind. While I had the engine out to repair bore scoring, I sent my trans to a shop in AZ to get the 2nd gear synchro replaced. It was shot. As he dug further into the trans, he found a tooth on the pinion gear was chipped and then he found the 3rd & 4th gear synchros were past their prime. I ended up buying a reman trans. Hope you have better luck with your repair.
Trans guy told me to replace the trans fluid every 10K mi. I do 2-3 DEs / yr. 10K mi might be a bit of overkill, I'm going to do 15K but that's way earlier than the 50K it had before I changed it the 1st time.
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GPRPCA Chief Driving Instructor
2008 Boxster S Limited Edition #005
2008 Cayman S Sport - Signal Green
1989 928 S4 5 spd - black
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