Automatic transmission shifting questions

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I have an 86 300e.
Ive owned about 30 cars in the last 10 years, but only 4 have been (GM) autos, so maybe i'm noticing what others already know to be normal.

When I drive the car cold in the morning (bringing the kid 1 mile down hill to school) the transmission seems to "stick" in gear. That is, when i move off from the curb and coast down hill, it doesn't coast up to 4th. It stays in 2nd.
It'll do the same thing all the way to school. If i goose it and let off quickly it'll shift up and coast a bit better. Even stranger, while still cold, and coasting, it feels like its not coasting all the time. It'll catch and let go catch and let go. The RPMs arent affected, but you can feel it. After about a mile it warms up and operates fine.

Other than having a potential kick down issue, the transmission is pretty good feeling. It seems to have trouble kicking down (thanks to my adjustment probably) you have to floor it pretty much to get it into 3 and have to be going damn slow to kick it into 2. Other than that, when I shift into reverse, it kind of hits hard, but my idle is a hundred or two too high. So in between D and R it kind of revs making my shift a bit harsh. Shift ups and downs (other than sticking when cold) are smooth.

I've changed the fluid (that which was not in the TC) and filter. I run regular Mobil 1 Synthetic ATF, not some MB fluid, the guy before me had a jug of valvoline Atf in the back. (so i guess i have a blend due to not draining the TC) I have not noticed any change in the transmission since changing the fluid a few hundred to 1000 miles ago. Maybe save the kick down SEEMS to be different.

So, what's up?
Thanks a lot for putting up with long posts..