Now I know a pup is 28', generally. But when it comes down to it, a 28'er is not giving too much advantage over a 24' straight, other than weight. Now, what I call a pup is up to 40'. I don't generally compare them to straights, as the benefits are a given... or should be. I tend to compare them to traditional 53' trailers.
Arguments for a small to medium trailer vs a straight truck:
-Both allow you to turn around in a narrow area. Advantage - slightly straight.
-Both allow you to park in a smaller space. Advantage- slightly straight.
-Need a CDL-A for a pup vs a B for a straight. Advantage - straight.
-Restricted roads. Advantage - straight.
-Tolls. Advantage - straight.
-Fees. Advantage - straight.
-Insurance. Advantage - straight.
-Mileage. Advantage - slightly straight, depending on weight.
-Ability to drop your trailer while they're loading you over 6 hours. Advantage - pup.
-Repairs - slightly pup.
-Replacement components. Advantage - pup.
-Replacement vehicle availability. Advantage - pup.
-Sell-ability. Advantage - Advantage - pup.
-Transfer-ability into a new venture. Advantage - pup.
-Flexibility in loads. Advantage - pup.
-Rate. Advantage - pup.
-Profit. Advantage - pup.
-Having what the others don't. Advantage - pup.
Overall... I'll let you decide that one. It all depends on what you're after. But IMO, a T/T driver who wants to downsize, would probably be ok in a pup. What turned me off with the 53'ers is that they were 53', not that they were trailers.