New here looking for a TJ for my first Jeep

Is this the start of it or just paint peeling
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More including the passengers front suspension
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Is this amount of oil on the transmission and oil pan indicative of a possible issue?
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I know a 15 year old Jeep isn't going to be perfect I just want to make the most informed decision I can. Thanks again for all the help!
 
The top pic is a great angle. It looks like the start of delamination. Gone just past surface rust.
 
It will be hard to find a completely rust free Jeep where you live but not impossible. A little surface rust can be worked with but once the frame has started the delaimation process it's best to walk away.
 
I'm going to see the 06 with 33k miles tomorrow. If it's really as clean as it looks from the pictures (even the ones from under the frame) maybe it's worth the extra $6k. It'll stay relatively clean as well since I will always have it garage kept. Also, this is going to be my daily driver if/when I get one. I don't plan on much more modification and definitely not a rock crawler or anything. If that is the case would the 5 sp and Dana44 rear end really offer much of an advantage to me?
 
I'm going to see the 06 with 33k miles tomorrow. If it's really as clean as it looks from the pictures (even the ones from under the frame) maybe it's worth the extra $6k. It'll stay relatively clean as well since I will always have it garage kept. Also, this is going to be my daily driver if/when I get one. I don't plan on much more modification and definitely not a rock crawler or anything. If that is the case would the 5 sp and Dana44 rear end really offer much of an advantage to me?
The Dana 35 for a DD and mild off road is good. A lot of those on here run them. You run into trouble when the tires get too big and the abuse off road gets out of hand.
 
I would go with the 02 if it wasn't rusty. Otherwise the least amount of rust wins.
I couldn't justify spending that much money on the red one. Mostly personal preference tho. I don't like the look of half doors, red vehicles, halos or chrome :-). It might be worth it in the jeep community. Unless you do alot of highway driving, cruise controls isn't something to base a decision on. Low miles is nice but I consider 150k miles on the 6 cyl as low miles :-).
Good luck and welcome