Backroad Explorer Build Questions

Not doubt winches are useful overall and more so the more trees there are around - either as anchors or when you need to move them out of the way! In general weight is better in the bed than on the front. The GAWR for the front is lower than the back and the truck starts closer to the limit on the front already. That said since you are looking to just add a winch to the front and not a heavy steel bumper as well I don't think you need to worry about it much one way or another - front mounted option or something you carry in the bed should both be just fine.

Also, since you are a Sport and sticking with a stock bumper look into getting the stronger front recovery point that comes on the OR. It bolts right onto any trim package of truck and is strong enough for recovery. The wimpy little loops on the non-OR trucks are only meant for securing the vehicle on a flat bed and would probably rip off the frame if used for actual recovery.

Lots of people like nice wheels, go for it if you like it!

I think Bilstein 5100 is probably a great option, also consider the 6112. Check out @Crom's amazing build thread where he has spent a lot of time going over his suspension design which is probably really well suited to your goals. Link's to all the various stages of his suspension experience are in the first post of his build thread.

Don't drop the diff. On a second gen it does little to nothing to improve the CV angles and can have some negative side effects. Sway-bar relocate depends on the particular coilover you end up using in the front, but for many after market coil overs the answer is yes (and some even include them).

One issue with add-a-leaf is that the stock springs really just suck beyond words and so it might not be the best long term solution. You might be happier long term replacing the springs entirely (Dakar a very popular option). Really depends a lot on how much weight you will carry. Keep in mind the stronger you make the springs for camping loads the rougher the right empty will be.

Usually there are few issues with a 1.5-2" lift. The most common issue though is driveline vibrations from a rear lift. The amount of lift in the rear really depends on the load and so it might be 1.5" loaded for a long trip and almost 3" when empty. When at the higher end the driveline angle can get far enough out of whack that you get vibes - very common issue. The solution is to improve the driveline angles for the new lift height. This can be done two places. First by lowering the carrier bearing a bit. Super simple, just add spacers and slightly longer bolts. Second by angling the rear diff up a bit, this is done with angled shims that you bolt into the leaf pack. The CB drop is easy to add any time, the shims are a pain because you have to remove the leafs to add it. So most people going to the higher end of the lift (say around 3") will add the shims right from the start when installing the springs.

Anyway, lots of info on suspension here on TW. Really too much honestly, easy to get confused. Just remember some folks are building to drive 60 mph over giant whoops. That's not you (or me). Others want a more comfortable and capable off road rig for access to camping and hiking. Different users have different needs.