I had an F-150 regular cab 4x4 with an 8 ft bed (and topper), then went to a Tacoma 4x4 extended cab with a 6 ft bed and now have a Tacoma crew cab 4x4 with a 5 ft bed.
The F-150 long box was awesome for the rare occasion when I needed to haul a ton of stuff and rocked for long camping trips but parking it in town and buying gas (10mph) was NO FUN!!
My Tacoma extended cab with the 6ft bed was awesome off-road and in town. It was perfect for hunting but a tad tight for long camping trips and hauling and too tight for a family with kids. With the tailgate down, it could handle a half dozen 4x8 sheets of plywood with a bunch of studs but it definitely wasn't designed to be a "work truck". That being said, I drove it to/from work and around town 95% of the time and it was ideal for that (20mph).
My current Tacoma crew cab 4x4 is GREAT for hauling the family and works for short trips and/or hunting but that's about it. I would never go with a bed this short again!!
If I were buying a new truck today, I'd either go with a Tacoma crew cab 4x4 with the 6 ft box or a Ford F-150 crew cab with the 6.5 ft box. Everything's a compromise but either of those two would probably be the best match for what I do.....
