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I ditched my 09 single cab with 200k for an 08 ext cab, 4wd, cap, with now 63k. I owe $12k on it. The bed sides are rusted and I purchased a new bed for $1500 and found out the new bed needs a side and will cost $4k to complete. Rockers also have surface rust. I found a 2016 grand cherokee with 63k miles for $23k. Kbb Fair for my silverado is $13k. There is a large part of me that says ditch the truck and get into something with the same miles and newer. This is only my 2nd vehicle and the 09 was purchased brand new. What would you gents do and why?
 

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1999 Silverado ECSB 6.0
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Keep it. If it is just the bed that is screwed then find another one. Get the surface rust taken care of on the rockers and get them future proofed. Start getting the frame taken care of as well. You owe $12k, KBB is over shooting so you probably will only get $10k, then you are in the hole for $2k and then in the hole for $23k. Even if you get $13k for your truck congrats you are in the hole for $22k.

If you can fix what you have then drive it into the ground.
 

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I would be more careful next time when looking for a vehicle.
 
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