The proper way to check the tranny fluid, per the owners manual, is to bring it up to operating temp, set the emergency brake, and run it through each gear (RND...I do 1-2 and 3 as well), then put it in Neutral and check the level.
As far as the problem goes, mine is doing the same thing and its about to drive me crazy! I can drive it 35 miles down the highway, let it sit at work for 8 hours, and drive it the 35 miles back home at 100* temps and not have a problem. However, If I go to run any errands on the way home from work, or get stuck in stop and go traffic, it will begin to leak and coat everything underneath, as well as make a mess in the driveway. It will also start to do this if I drive the highway trip and turn around and come right back (with no break, or very little of one).
For now I just deal with it, and degrease everything underneath as it happens, so that it doesn't drip all over the driveway for days.
edit: ebxjbob, did the 97 you had also seem like it "slammed" or "jerked" out of OD when you took your foot off the pedal? Mine will do this if I take my foot off too quickly, and I believe this is aiding in the fluid leak.