Re-Use 220k Shortblock?

[Supercharged111]

You should ideally be dropping the oil pan. I used a Cloyes single roller adjustable timing set on my 1500, for the dually I just threw a new GM chain on, but I think that was roller too. New timing cover comes with front seal, again I went GM there.

 

[Jeepwalker]

Did you say it was on an engine stand? Just rotate it as you're working so the crud is falling 'down' ..and then block off, or tape a shop towel in areas to keep it out of the rotating assembly. Might have to clean the block with some carb cleaner to get the tape to adhere. And/or use a shop vac to suck away the debris. If you have a floor or upholstery attachment for the shop vac, rotate them (facing 'up') and hold below where you're working so you have a larger suction area for the debris to fall into as you clean it up. sorry if that sounds confusing.

Yeah, I guess if your oil pressure was good, maybe leave the bearings. Mine has 265k and afaik the engine's original (but I'm the 3rd owner). It's possible it was replaced but it never looked like it was.

 

[Erik the Awful]

Lots of good stuff. Here's the TL;DR so far.

If the oil pressure was good, and you're cheap like me, keep rocking the same bearings. I wouldn't even bother checking the clearance.
--- If the oil pressure wasn't great, I'd replace the bearings and check the clearance.
Replace the timing chain. Spend a little money on a name-brand. Personally, I think the stock link-type are just fine.
Check to make sure the oil pickup is set at the right height, and then put a tack weld on it or braze it.
Replace the front and rear seals. I've successfully reused the plastic timing cover with a little dab of sealer in the corners, but a new one's only $20 on RockAuto.
Replace the freeze plugs if they don't look new. Around here I'd just check them, but you're in Michigan.
Flush the coolant passages until the water comes out clear.
Check the oil pan condition.

The water pump is your call. They're easy enough to replace that I'd only do it if mine were seeping, but you are right there right now.

 

[Supercharged111]

Lots of good stuff. Here's the TL;DR so far.

If the oil pressure was good, and you're cheap like me, keep rocking the same bearings. I wouldn't even bother checking the clearance.
--- If the oil pressure wasn't great, I'd replace the bearings and check the clearance.
Replace the timing chain. Spend a little money on a name-brand. Personally, I think the stock link-type are just fine.
Check to make sure the oil pickup is set at the right height, and then put a tack weld on it or braze it.
Replace the front and rear seals. I've successfully reused the plastic timing cover with a little dab of sealer in the corners, but a new one's only $20 on RockAuto.
Replace the freeze plugs if they don't look new. Around here I'd just check them, but you're in Michigan.
Flush the coolant passages until the water comes out clear.
Check the oil pan condition.

The water pump is your call. They're easy enough to replace that I'd only do it if mine were seeping, but you are right there right now.

If oil pressure wasn't great, I'm leaning more toward worn cam bearings than rods/mains.

 

[Jeepwalker]

Water pump seals dry out when sitting if there wasn't coolant in it (which I doubt there was). It's a roll of the dice, but if you don't mind changing it on the truck ..hard to say how long it'll last. Could be a month, could be 2+ years...