Most people have no problems getting transport to work with any MIDI device. As long as the device is really MIDI.
NI has decided to drop MIDI for controlling part in S 2 keyboards. I do not know how it is with A. If MIDI from transport buttons is working, it can work in Cakewalk (it theoretically should, but not sure in current firmware/future or with extra NI bridge...).
Generic Surface, ACT MIDI, AZ Controller. Any from these 3 plug-ins can do the trick for any MIDI device (AZ Controller also can do this with OSC, so for S2, but no one has done that so far).
How hard can it be? At most deleting not existing devices in Windows device manager, deleting 2 files in Cakewalk and spending 10 minutes with documentation. Definitively manageable in 3 decades...
Ableton is a nice program. But there are not many people which use it instead of Cakewalk/S1/Cubase/ProTools/REAPER/etc. Ableton has specific workflow targeting specific purpure, people use it in addition to conventional DAWs (when they need related functionality).