What I’ve found is people will never pay for good upkeep. Unless it’s a situation where the buyer has a relationship with the seller and knows the history. When we sold my dad’s 92 K1500 in 2015, I think we started at $6,500. Keep in mind this thing was in showroom, original condition. Brand new 265/75/16 Michelins, 165,000 miles, new goodwrench 350 and 4l60 both installed at Chevy dealership within last 30,000 miles. It had never been worked on by anyone besides dealership, my dad(actually worked as a mechanic at Pontiac dealership in late 60’s before being drafted) and myself. No bites at $6500. Quit trying for a while. Then listed again at $5,500 I believe. Also parked it out by the road with sign(rural farming area). Literally within 5 minutes farmer from area drives by, stops, backs up and pulls in. He says let me grab my check book, Are you sure $5,500 is enough? He knew what he was getting.
When I bought this 88 last year, I wasn’t really looking but it just popped up. I was more drawn to it having the options I wanted before I saw the low miles. Blue interior, Silverado, 9.5” 6 lug rear end. It was beat to holy hell for only 49,000 miles. But I know enough to know I could work with it and make it exactly what I want. He was asking $5,500. I paid $5,000. From an outsider’s view, I think it was only worth maybe $3,000.