I have to say, since working on a 99 Challenger right now the factory windline ladder is DA' BOMB! Being 6'-2" 230# I can put my feet on the last rung and just pivot and lay across the deck and work on the engines perfectly. The rubber strap was broken on this one as well at one point but replaced with a heavy duty piece of webbing with a snap.
Which one are you looking to get the UP-2? If so that is the exact same one on the one I have here and those other brackets look the same.
The brackets measure 3.125 center to center measured across the bracket and 1.250 front to back. Which I'd bet are the same bracket. You can't use a longer bracket do to the way the glass is molded. There is also a flathead screw with a washer where the end of the tube will apply pressure to the boat and not dig into the gelcoat. If you need pics let me know.
So the UP-2 is $95 and the brackets are another $30, plus shipping. So you like 1/2 the cost, not shabby.
Not sure what the hang up is (other than the cost) on the Windline ladder. I have the same one on my Speedster. Personally I couldn't imagine a single step to get back in with it would be awkward as all get out an I have two really nice handles in the back of my swim platform that the Challenger does not have. I know you have a couple of years on me (I'm 38), but with a single stepper you better be a world class gymnast or a Russian contortionist to put your leg over your head to get out of the water. LOL