You'll probably need to drop the skid plate that's right under her Runner. The filter may be a bitch to get off though, but you should be able to. If you you are having trouble (I'm not sure if this will work on newer Runners), turn the wheels to the left and go through the wheel well on the driver's side and you should be able to get a hold of it that way.
Synth isn't mandatory, but it wouldn't hurt to protect her investment. 5-30 should be just fine and no, you won't need to use jackstands. You can just slide under there and do all the work. I would stick with OEM filters, but if you get aftermarket ones I would go with Mobil 1, Amsoil, Napa Gold or Purolator PureOne, but whatever you do don't get Fram. And yes, there is a crush washer that will need to be replaced after each oil change that you can get from the Stealer for a few cents.
That should cover it. I would also suggest you head on over to
www.yotatech.com because there are a bunch of guys there with mostly Runners there and can give you some great advice there without all the unnecessary flaming and banter. A great group of guys and gals too.