As for your upside-down steering wheel, this happened to me twice, once when I slid off the road and smacked a curb, and once when I slid off the road and smacked a tree. In both cases, the front tire(s) struck something solid while the wheel was turned. My jeep was at both times a manual steering jeep with 31" tires. The first time, I replaced the steering gearbox. The second time, the jeep was just a toy, so I unbolted the (Grant) steering wheel and rebolted it in the new center position. I finally swapped in a power steering system and have not had problems since, but then, I haven't slid off the road into something solid, either.
With respect to the DW problem, honestly, I've only ever heard people complain about it who have old, high-mileage or otherwise well-worn jeeps, and none of them has done any preventative maintenance on the front end components. If cash is tight but you're not strapped, do yourself a favor and replace all bushings, ball joints and tie rod ends. You're not talking a lot of money (unless you go to the Jeep dealer for the parts... new tie rod end at Jeep in Indy, 85 bucks, 13 or 14 bucks on-line), and you'll have peace of mind knowing your front end - your ability to steer, the most important part of a vehicle, IMO - is good and tight and ready for another 50k miles. Good luck -
Edit: I drove for many miles on 33s with no steering stabilizer. The jeep darted all over the place, especially under braking, but never went into the DW. I finally got around to ditching the 4WD Hardware dual stabilizer setup, which was rusted out, with a new factory stabilizer, and the old dog was a whole new vehicle, tracking straight and true under all circumstances.