I don't think anyone else's experiences with their trucks is really relevant as he didn't ask for truck opinions. He had the experience he had with his and it is obviously causing a bit of anxiety.
I don't know how picky you are about things Freedom, everyone is different. But a couple of drops of oil on an old truck really isn't anything to fret over. If you have a big puddle, then sure I get it.
If the truck isn't giving you a warm and fuzzy, I really don't see how you arrived at the $100,000 mark as you can get a slightly used diesel 3/4 ton short bed, crew cab for $40,000 or so easy. Gassers and non-crew cabs are even cheaper.
I really don't want to throw fuel on the gas vs diesel comments, but people who spout off nonsense about diesels costing more to repair don't know what they are talking about. There are horror stories on both sides of the fence, and there's the majority that are common.