I've run 33's and 3.73's for a few years now, with an auto trans and I live in a hilly area of Kentucky (not the mountains, however).
The 3.27 speedo gear is really close. one more (or less?) tooth and it should be spot on. My speedo is 10% off, 50 is 55, 60 is 66, etc.. This is observed with a good GPS to compare against.
All A4LD trans need a good cooler. This tire/gear combo needs it too.
When starting up a bigger hill, tap the brake very slightly. The tranny should drop from overdrive to drive and unlock the TC. This type of downshift before it gets under a heavier load seems to be much easier on the trans, plus you don't lose speed before a forced down shift half way up the hill.
Turning the screw in the modulator valve will delay shifts some, it can really help. A shift improver kit for towing *really* helps, and that is an extremely good idea for any A4LD tranny anyway imho.
33's and 3.73's is about like driving a stock tired truck with the tall gears (3.27). Mine is great on the Interstate and drives very good in town too. It's not a sports car of course.
Some of the conventional mods like exhaust and air intake tweaks can really help the low end power/torque, that was the biggest improvement I ever did. That helps my MPG too. I get about 16-18 depending on conditions. MPG drops at 75mph in the Interstate obviously. A 1st gen Explorer with a 6" kit and 33's is shaped like a concrete block basically. heh