I recently picked up this 83 that is clean underneath and has been repainted before me white but has some surface rust around the door channels and in the bed. Do i need to repaint this? I know it would look better but i personally like the rougher look and don't want to drop 7K. I plan on keeping it for a while as a daily driver and now it's in the wetter East Coast.

 

That rust on the cab is from the gutter seam sealant being cracked and half gone. It will rust from the inside out. You need to wire wheel the gutters, remove all old seam seal/rust, hope you don't have holes and reseal/paint. If you let it go, it will get to the point the cab wont be salvageable. A urethane seam seal, like this, is what was recommended to me
I don't see anything concerning going on with the bed.

 

Fix all the spots that even vaguely look suspicious. That rust is just holes waiting to be born...take it from a guy originally from eastern Canada, we know rust!

There are some seams above the fenders in the box that look like its getting a foothold. There is a seam above the rear marker light that looks suspect. Check under those box rails and under the carpet around the front body mounts.

You can fix it up yourself. Start with the inside of the box to get practice then move onto the more visible spots. Don't trust the colour code to mix the paint, go to a place that has colour chips and match it that way. With a white truck do this on a cloudy day. The white paint will dazzle your vision and be hard to match on a sunny day. When its done or even now, because your in a wetter area get it oil sprayed...Rust Check, Krown, Fluid Film, doesn't matter just do it or within 5 years it'll be rotten. Do frame too, outside and more importantly inside and check all the drain holes.