Diagnosing transmission problems

Car is a 2001 Regal LS, 37,000 miles, original ATF (level is fine).

I've recently noticed a couple issues that seem to be transmission related. I'll try to describe them as best I can...

1. My driveway includes a short flat part and then a hill up to the parking lot. I generally have to hit the gas partway up the hill to clear it. When I do this, I get kind of a shudder or skip, as if the transmission was not in gear or between gears, and then the gear engages.

2. My commute is through stop-and-go/highway traffic. One thing that often happens is slowing down to an almost stop, and then accelerating. If I slow down to approximately 15-20mph and then accelerate, I again get the shudder or skip, and then gear engage, as described before.

3. This may be normal, I don't know: either 4th gear, or the torque converter lockup, doesn't engage until approximately 65 mph. I think it's 4th because there seems to be a larger than described RPM drop for it to be the torque converter... but what would my RPMs be at 65 in 3rd?

I guess what I'm mainly wondering, is are these things normal? If not, how would I describe the problems to a shop?

You will only get TCC lockup at speeds above approximately 45 mph and in 4th - OD only.

As for the shudder possibly a line pressure/PCS (pressure control solenoid) issue. Get it scanned with a trans capable scan tool and see if any tranny related DTCs are stored.