im gunna go with 5000 pound badland winch from harbor frieght. pay the extra $35 for the no questions ask warranty. there winches are just as good as the more expensive winches. i know some stuff from harbor frieght is junk but these are good. if you use your winch alot they take a beating and once you get close to your warranty being up you take it in a get a brand new one. i have run the 3000 pound winch on my foreman for a couple years now and its held up good and pulls hard.
For that price you can get a Superwinch Terra 45 and not NEED a warranty!
But as for the OP's questions-
I would go minimum of 4000lb. Keep in mind winch ratings are at BEST, and with a near empty drum. That being said, I have used my Terra 45 (4500lb) quite a few times so far, both pulling the Honda out of snow, and over downed trees, and also pulled vehicles up hills and through ditches in wooded trails. I do plan to build a snatch block (rope sheath for $5.99, cnc cut brackets and a pin!) to carry this spring when the mud gets bad, as I could see it possibly being needed with a bad stuck/ retrieval of a larger stuck vehicle.
I bought the winch with wire rope due to cost, and damaged it the first use (inexperience with winch). I replaced with synthetic, its far, far better in every way. I actually just picked the wire off the shop floor a few days ago trying to clean up, and cut my finger trying to roll it up, even cautiously!
The Terra 45 comes with a wired remote, which comes in handy on occasion, but not exactly necessary. Perhaps more important if you wheel alone?
. Wondering what size the pioneer 2 will need. I am thinking 4000 will do but the 4500 would be better. I like the synthetic rope option. Remote control, is that option just a luxury? Warn verses superwinch verses viper will be for another day. 
