285/75/16 is about a 32/33" tire 5.29 is a large jump. probably more gear than you want for a street truck (no picture or any real info other than asking to be told what gear to run) a quick search will find many gear calculators, figure what your stock final gear ratio is and work on matching it. And yes running 4 or 5 hundred more RPM will help with a heavier rig.
On a 22re/ manual trans with 35's Im running 5.29's its primarily a desert/ rock crawler. very minimun street use. It's very quick stop light to stop light, but really spins the motor on the highway. I did it for final crawl ratio.
my other rig is a 3.4/auto on 37's running 4.88's and at 65 in overdrive it's at 2K on the tach, that truck actually could use 5.29's but with the auto it wheels good, and 4.88's have more meat to the gear.
find a gear ratio calculator, run the numbers, then come back and ask guys running those gears what they think.
You will have a better understanding of where you were stock, where you are now, and what you could expect with a gear change.
also is it cost effective to really make the change.
Just my opinion!