dcloud is no longer related to dSS, it's all self hosted now. I've not made multiple versions of the installers...however it makes me wonder because each file name is usually "dsupport.exe" I wonder if it's getting confused with the same names. Personally what I would do (you may choose differently)
-create my installer
-upload manually to ftp (its own area)
-create an "app" that links to that file instead of using the built in feature of the dSS button (save that for the other version)
As for d7 vs d7ii I went back to d7 recently and it made me want to drive a knife through my temple because i'm so used to d7ii lol. Speaking of i'm actually writing up a couple of tutorials for d7ii, and a couple of my secret tricks I do with d7ii and my flash drives that you might be interested in. Because d7ii can be a bit overwhelming when coming from d7 because there are a lot of things different...and everything is a HUGE improvement. You can expect to see them in the next couple of days....I might get bored enough to make some videos also.
If I had a world of my own, everything would be nonsense.....Who in the world am I? Ah, that's the great puzzle. I'm afraid I can't explain myself, sir. Because I am not myself, you see?