Coolant Leak Issue, Need Help

Hello Folks,

So this isnt an A-body, but a 1990 Dodge W150. It has the trusty LA 360 and I noticed a coolant puddle forming on the floor around the front of the engine. My dad purchased this back in 92' with 55,000 miles on it. in 1998 it received a Chrysler Re-manufactured engine and a new transmission at 101110 miles. it currently has about 208,000 miles.

I kind of commandeered the truck (since it is my fathers "back up" truck now) after I purchased a house. So I bring it out here in mid December and drove it for a little. Last I drove it was the week before Christmas since the weather turned cold and the roads went white with salt. I started to notice a small puddle forming under the front of the engine after I didnt drive it for a week or so. I didnt think anything of it since my dad said it had an issue with the timing chain cover leaking. A master mechanic at a Chrylser Jeep dealership that races a late 70s Volare had a similar issue with the 360 he put into his car. He said he just changed the timing cover and the problem stopped. According to my old man, at the time there were two timing chain covers one for $60, and one for $160. He and the master mechanic got the $60 one and installed it. This was back in 2014 when the truck had almost 193000 miles (engine had about 92,000 at that point). Prior to that he replaced the timing chain in 2011 when the truck had 184500 miles on it (engine had about 83,000 miles on it at that point).

So this leaves me to what to do about this issue. I crawled underneath the truck last night and saw that although the timing chain cover was a little wet around the crankshaft port, it was nothing compared to the droplets of coolant that were on the oil pan to block flange. The radiator is dry, but the oil pan is wet. it looks like it ran down the oil pan flange, down the oil pan, onto the cross member, and rolled to the rear of the cross member before it dripped to the floor. The engine and cross member are pretty greasy, my dad isnt as anal about keeping the engine clean like I am, so it is hard to tell if the engine is only leaking from the timing cover, or else where as well.

Has anyone encountered a similar issue? Did you find a fix for this? Could something of changed on the engine block from the time he changed the timing chain (like something being warped? or the cover not being installed correctly?)? Why would it take another 10,000 miles for the issue to come to fruition again?

Though this is an old truck that is in reasonably good shape, it is still used to haul and tow stuff since it has a cap and an 8ft bed. Sadly I wont be able to do much for the truck for a month or so due to work related events but will try to aid in any questions you may have

thank you