Those with jeep transmissions going out with less than 100k on them, how often was the fluid changed on them, and did you use the correct mopar +4 fluid? Overall, both toyotas and jeeps are sound vehicles. Make sure someone decent works on them, and keep the backyard hacks away from them. Keep the oil changed in them regularly, as spelled out in the maintenance schedule. Though I have nothing against toyotas, I think they are highly over rated, and overpriced, and some jeeps fall into that ranking as well.
My Y2K Jeep Grand Cherokee has 182K on it with no serious maintenance issues yet. My wife's Y2K Grand Cherokee has 137K miles on it - we had to replace the A/C condenser on it back in '05.