Warning: this is truly a First World Problem thread.
Having owned many pickups I've learned they are nice to have around. I currently have one, but I'm not in love with it. My prior truck was a pretty nice 5-footer, a 1965 F100 Custom Cab I bought in NC (I'm in PA where they have all long evaporated). I owned it for ten years and really liked it but two things conspired that had me sell it. One, it had some rust issues on the exterior that would require expensive paintwork (the usual undercarriage issues were not present). Two, I'd moved from just playing with track cars to racing them and needed something better to tow with. While the old truck did fine I had some issues with the column shifter (surprise) and vapor locking. Coupled with the manual steering, no a/c, etc and the charm was quickly vanishing.
I wound up buying a '93 Lightning (non-SC model) and sold the '65. The Lightning had all the power toys, real cloth seats, a/c and auto trans that made towing not hateful. It has not been without it's issues, however. Reliable, but annoying fluid leaks and a particularly poorly placed cab water leak (that I think I finally fixed) made me not love it. This one came from KY and has not a speck of rust on it but the non-clearcoat red paint is beyond reviving with a buffing pad. The truck also has 170,000 miles though it uses no oil between changes. While it does have electronic ignition and EFI it also has a computer you can't buy anymore as well as some Lightning specific unobtainium parts that cause worry. I bought it right and it has doubled in value over the time I've had it. Much like some cars, this truck and I have never 'gelled' and I could cheerfully sell it tomorrow.
As much as I like the 65-66 trucks like I had before there are certain parts issues I'd rather not endure. I like stuff that is cheap to fix and easy to get things for. I've been browsing mid-70s 'dentside' trucks as the styling appeals to me and they are essentially the same underneath as my beloved '65. And, you can buy virtually anything for them. With a nice set of wheels I could make it look cool and would have something I'd be 'into'.
But, vintage trucks prices have gone INSANE. Stuff I used to pay $3500 for is now $7500. A good five footer is nearly ten grand. As a guy who can't abide rust and wants nothing to do with repainting a vehicle it's very hard to find a nice driver quality truck that isn't $15k or more. If I sold the Lightning I could pay for most of a five footer. If I could find one. Or, I just keep the paid-for Lightning for doing truck things (which, honestly, I don't do all that often now), let it appreciate more and hope it doesn't need an unobtainium part while wearing it's hopelessly faded paint.
Or, I sell it and just buy a utility trailer for the times I need to haul something.
Final consideration: the truck is tagged and insured as a collector vehicle so doesn't really cost me much to own.
ETA: I no longer have a need to tow a car trailer. Both race car and trailer got sold this past fall.