Was talking with a family member who works for one of the local power companies and they are replacing some poles and he believes he can get me one that is 30-40 feet long and will come with the work truck and drill a hole to put it in and stand it up for me but will give me time to mount the aluminum pipe the antenna will be on to the power pole
Typically utility poles are sunk in a hole several feet deep, so a 30 foot pole sunk in 5-6 feet won't put you much higher than your original plan of a 20 foot high antenna.
I know this might seem odd but will it being that high extend my range of options of what I receive compared to having it at about 15-20 feet off the ground
Depends on how much higher it actually is. 3-4 feet, unlikely to make a big difference. 10 feet higher, you'll probably benefit.
Since most of the frequencies used (VHF, UHF, 700, 800MHz) are mostly line of sight, the higher you get the antenna, the farther over the horizon it can see.
A good condition pole installed by professionals is a pretty sweet setup.
But consider the cost of renting a lift if you need to repair or change your antenna setup. Unless you know how to climb poles, it can get expensive (unless you buy your buddy lunch and have him bring his bucket truck by…)