It's a tough choice for sure. If my truck was a half ton, it's be worth a lot more. Most people want the half tons so they can trick them out. Realistically it's around 5-6k in value. It's not perfect, has some rust in the front fenders, and it could use a new paint job. I did redo the interior though. I think in the future it may need a new clutch, and the bed wood is starting to give up on it.
The 300 has the buckets and the leather is in ok shape up front, but needs attention in the back. The STP sticker I was told is covering a blemish, and one of the back windows won't roll down. He did just have the motor gone through, no leaks at all now.
If I had bought the truck from someone, I would have no hesitation, but it's a shame how little I drive it. I'd drive the 300 more for cruising, more fun than driving a dump truck style transmission.