98 Truck questions

I agree with covering up an issue but ive seen very close ups and this appears to be just an ugly coating of what looks like a bed liner type paint that has worn off a lot over the years. But believe me I will look very close before I buy because I dont want someone elses rust bucket. The only reason I am looking at a small wheel base is because I want to keep it in my garage and I also will only be towing about 35-40 miles at a time with the exception of once a year if I would decide to go to the car show at ocean city md and that would be 165 miles one way. I will try posting some pics of it later tonight if I get a chance. I thought maybe if I get it I would install a shift kit. Would that help to extend any longevity in trans. He says it shifts great but ive heard that many times over the years. Also will need to install a trans cooler although he thinks it has one now.
Keep your thoughts coming as I may need to make a decision on Tuesday.
Thanks Rod