To be fair, I'm not a winch nerd, but when I see someone with a Warn winch, my thought is "they spent a hell of a lot more money for their chinese winch than I paid for my chinese winch" 😆
The only need to modify it is when you run into its stock limits when off-roading. Sound like thats not been a problem for you, and that's fine. Don't feel pressured to do anything to it.
chat gpt can tell you which gears to use, the benefits of regearing, and exactly how to regear your jeep but is absolutely stunned when you ask the very simple question, "What is a woman?"
https://s3.amazonaws.com/rp-part-images/assets/97d631a967270c28e761ee8a5a65c56b.PDF
In the install instructions, it has the part number for your application. Google that number and you will find the replacement part from Mopar
There's nothing complicated about that.
1) Fill.
2) Start car (jeep), check level.
3) Add as necessary.
Literally no different than any other A/T trans fill.
The price difference is SUBSTANTIAL between new d44s and 1 tons. Another thing to consider is wheeling style. Is the OP going to be full throttle rock bouncing? Probably shoulda got tons. Literally any trail in Moab? d44 (m210/m220) and 37's is good enough.
A Sport with the m220 housing has a spline count and tube thickness that is identical to a rubicon. It's 1.5 inches narrower. Nobody will miss 1.5 inches. Not on the trail at least.
Parts under warranty is overrated. All that means is you will be afraid to upgrade/work on your Jeep because the weasel dealership might deny any more work.
The tube is broken? I've got a m186 housing you can have for free if you can get it from Dallas to TN. Slap all your old guts in it and be back up in no time.