Unless the Mrs is an amazon, she will have an easier time with the 33s. I would also add the slee step sliders or a comparable homebrew slider system. The pulling to the right may just be tire pressure. If you don't have birf soup, there is no reason to tear everything apart. Just add grease through the fill hole and adjust the preload on the bearings.
The factory lockers can be finicky without regular use. Just turn the dial all the way and do figure 8s for 10 min, they will likely engage as long as the center is locking. Just remember, no center lock=no axle lock unless you get creative.
Doing an axle service and doing a regear are two completely different animals. Also, since you have the factory lockers, aftermarket gears are harder to find and more expensive.
I would stick with 33s, 285 or 305s with a 255 as a spare. Unless you will be installing a bumper with a tire carrier, you will want to retain the ability to keep the spare in the stock location. Putting a 35 inside takes up a lot of room and it is a lot of weight to throw up on the rack. (COG issues+having to lift it up there) The 255 spare is a lot easier to handle and is skinnier to increase clearance.
I have 5 critters of my own so I feel your pain, but the third row isn't really necessary, and you could build a sleeping platform back there for the you and the wife or the kiddos. (A queen size air bed fits perfectly.)
I would go with OME Heavies due to the planned front and rear bumper/winch/rack etc.
FWIW, my rig has TJM heavies, slee sliders/skid plates, ARB, smallish rack and 285s so I may be partial to that particular build. I wheeled a couple times with guys on 35s and was able to get through everything they did--it was just harder. For Expedition wheeling, it won't be an issue---many, many, many 80s have done moab on 33s.
As for the winch, I am a cheap bastard and will be going with the HF/Chicago electric or the cheap costco winch. Milemarkers are not bad, but they are not much better (if any, depending on model) than the cheapo winches.