What something is worth to people is subjective.
I like the 2010.5 with the 6.2 because it has less "upgrades". No automatic seat a^s wiper comfort control module to replace..
It also depends on aftermarket parts when you get to the older trucks.
Why? Because shocks, springs, control arm bushings, headlights and bumpers will all be worn. You won't get what you put into most vehicles on aftermarket parts. It will however be worth more and more useful than an older truck with blown-out shocks, flat springs, busted sunroof tracks, melted fuse 27 etc.
Even frame chop bumpers vs stock replacement for rusted is better than rusted or bent stock bumpers.
I buff out the paint on my 2010 and with the Morimoto LED lights LED replacements all over, 2017 wheels... People who aren't truck people think it is a 2019 even raptor people think its the youngest 1st gen not the 1st year. With the upgrades, offroad I can all out wail on it, it takes it and my insurance at my age is $40 a month.
If someone is a real legit mechanic I really think you can buy a good 1 gen with 160k on it, build it a bit and beat a 2nd gen raptor everywhere but 0-60 all without car payments.
A friend test drove the cheapest used 1g around here in so-cal and then a lower-priced 2G. He only got to hit some speed bumps but he said neither rode like my 1g. I just showed him the pile of parts I replaced from one end to the other, both bumpers. all shocks, all springs, all lights, reskinned the seat... etc..
OP congrats on the reup with the Army. I did that a few times too... If you have skills and auto craft shop access, get a good 1st gen, year isn't important, clean carfax, service history, actual condition. One with just even properly installed Deavers is better than without. What are you really getting and what shape it is in is more important than MY'.
If you don't have the facility to work on it, I'd hold off until your last ETS.