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1) The sprag t-case works fine. They're a little fragile, and very intolerant of rolling backwards while in a forward gear. My understanding is the only way to go to an air shift t-case is a t-case swap. I've been stuck in a truck with a sprag t-case and it turned all 10 wheels in forward and...

When you lack enough experience to develop opinions of your own and you're forced to make decisions relying on the opinions and experiences of others, it is best to solicit opinions from as many sources as possible. (Referring to the OP) I've had a bunch of these trucks (5t and 2.5t) with tires...

Others' opinions regarding 395s on stock rims - https://www.steelsoldiers.com/threads/395s-on-stock-5-ton-rims.100979/

The deuce is really impressively capable even on 9.00 NDTs and open diffs. There's also something to be said for 5 spares instead of one. If your current tires are serviceable, I'd delay a tire upgrade until you can go all out on it. Just my opinion.

395s are designed for a wider wheel. I strongly advocate against it, although I have seen it done. My choice would be MRAP rims and adapter plates. If you must remain with the stock wheels, consider 11.00's.

I like the winch... Brakes are the first thing to examine in detail.