1. The transmission on the 87 is supposed to have a little 2-3 shift flare unless its not running properly. It depends on how exaggerated it is, in regarding it to be a problem or not. Sounds fine, unless it really bothers you. Definitely change the ATF and filter regardless.
2. The A/C vent problems can be CCU related or vacuum related. I would replace the vac switch solenoids (or whatever they are called) behind the glovebox, first. Then look into CCU, probably cold solder joints.