If you already have a standard hitch then the sidewinder is a great idea. Just know that if you sell the trailer the pin box usually is not easily transferrable or resellable. Superglides are.
I have full timed for 5.5 years now and the superglide is an amazing investment. Could I have made it work with a standard hitch? Most likely except for that one time when I had to pull a 180 on a two lane due to a closed bridge... probably would have forgot. Add in the cost of a new rear window and cab damage now you have the difference. Then there was that other time when the gps took me down a neighborhood street that dead ended, yep superglide came in handy there too.
Superglides can be found for $600-900 used in like new shape. Sometimes you can even get the mounting kits along with. If you plan on keeping the shortbed truck(s) longer than the trailer then your issue is answered.