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Just depends on the overall use of the truck, and owner preference. I prefer a stepside for a "street" truck. But I'd go a straightside LWB for a work truck, camper, etc..They made a LWB stepside, which I kind of like as far as looks. If I ever were to ditch my ute bed, I'd like to go with a long stepside if possible, if I had no plans for a camper shell. But they are sort of rare. The straight beds are a-plenty in comparison. MK
Your question askes about actual market value, as opposed to people's personal tastes.
I believe that from a market standpoint (as in, what will bring more on eBay, all other things being equal) the stepsides are more "desirable". They are by all means rarer. I suspect that just as many or more people like the styleside, but supply and demand will jack of the price of the stepside due to its relative rarity.
It seems like you see a lot more stepside chevys than Fords. I prefer the styleside for looks but the stepside is easier to fetch things out of. If you do get a stepside try to get the one with both fenders the same and not that notched out spare tire carrier. I would love to get my hands on a long stepside for my F-250. Back in the 70s they made toll boxes that bolted on in place of the fenders making them a low utility bed. I had one of those on a 73 F-100. Now Ford has it's own version that looks almost like a regular bed.
The thing about stepsides is the beds get dented on the sides less from other vehicles. Having a flareside is just asking for a dent that shows. Most people will have trouble denting your fender flare or step.
Willowbilly
My dad has a 69 long bed stepside converted to the low utility bins. It is the greatest for tools and u can still lean over far enough to get stuff out on a tall day. Between him and I we have only seen 1 other the same as his. But as far as looks it has it's own compared to any other 67-72's. His truck is in every photo of a 67-72 crew coming home to my house because it is always reliable and always has all the tools needed for repairs and towing-hauling my junk around. After having used his truck for a few junkyard trips it's kinda hard to like a styleside due to the fact that it can hide alot more goodies when going yard to yard on a Sat.
I have seen a few over the years. I worked at a GMC dealer back in the 70s when I got out of high school and a local maintainence guy had his switched to his new pickup every 2 years. Also a friend of mines dad had one on a chevy.
I had looked long and hard for that setup and when the 73 came along I jumped on it. It had a very tired 300 with a rebuilt auto laying in the back. Of course I didn't realize the engine was tired until I got the tranny in. By that time I had discovered that the Anchorage winters had done a number on the tool boxes and they were in bad shape inside. Then another guy came along and just had to have it and I made a couple hundred and let her go. I sure wish I could find a nice one now for my work truck.