I am an old racer guy here, motorcycles and cars, new to jeeps, but tuned into motor power bands and gear ratios If I were making this trip and had planning on regearing later, if I had had the time I would think about writing down a couple things.
Take your current final drive ratio, look at the individual transmission gear ratios for each gear and multiply to come up with the number. For deciding what to do later with regear ratios, you can calculate each of your 6 (think you posted that) speeds to what would be equivalent of that number in each gear after your final regear changes and how that fits with your current motor torque/horsepower situation in real life.
Me, 98 4.0 5 speed having stock 3.07 gears, stock tires does not seem to click with others who have posted here suggesting keeping at least 3K rpm at all times. 3k in 3rd puts me at 55mph, a common speed sign around here, 5th at 3K flat and level in most of my driving areas would put me at about 102 mph. (had enough speeding tickets in life even with 4.56 gears on the street with my hot rod 64 chevelle station wagon, do not need more. haha) My "tractor motor" 4.0 pulls good at 1500 rpm (flat land) down the road and not lugging till it gets down to about 1200 at about 45mph slowing down where I shift to 4th. (Yep, drove a few motors in my life, know what lugging is, I have the feel. I adjust my constant speed prop by ear, then look at the chart to make sure I am OK) kinda same thing as re-gearing on the fly, haha
So, yep if you never use 6th or 5th and 4 low in first is too high, you might want to spend the $ to regear. If not, hell, I have had 3 speeds, 4 speeds. and now a 5 speed with a HI/LO I can do on the fly (different than my Suburban have to stop to shift) I just pick the gear that works for where I am. I drive 5th on the flat highway at 1700 or more and do not worry about it. Have one section of road to my house that is 4th about 3 miles. then 3rd the rest of the way in till I get to the hill just up to my house, then 2nd, then 1st to pull up the slanted drive, one of those "manual transmission" things, ya know? Pick the gear that works best.
OK, that was item one. now for number two. I am an old guy, worked on nitro race cars, rode loud motorcycles, shooting, loud music, aircraft, before anyone thought about ear protection. Someone mentioned ear plugs. Got me to thinking about noise cancelling headsets. Wondering how that might work.
Not the ones like in my planes, only able to hear what I have plugged into my aircraft radios, but the ones I use for shooting, or even the $15 ones from harbor freight I use for mowing. Blanks out the shots, but can have a conversation with someone talking with me, I train shooting a lot. Might blank out (attinuate) the background noise in my jeep, but if Barnie Fife walked up and said, "Whatch doing with those on" I could easily hear what he said. Hummm I am an old guy with loud noises adjusting my hearing, causes ringing in my ears. Shezam, I just considered this. Will report back later. Was out with a flight instructor one time on a cross country, asked why I adjusted the pitch on the prop. I stated it did not feel right. He called flight service, barometric pressure had changed due to a fornt. Prop, sound gave me the feed back it was trying to go up hill. Not much different than driving up or down a hill but in a different demontion.