Based on the topic: viewtopic.php?f=18&t=565
I was able to locate my user profile at:
C:\Users\<My Username>\AppData\Local\Chromium\User Data
I also answered issue 3 in full by copying it over to the IronPortable profile directory and overwriting all data and as a result I got a working portable version of Iron...
Issue 1 rears its ugly head again. I cannot pin it properly to taskbar. I can manually pin IronPortable.exe but running that merely runs the non portable exe which results in there being 2 seperate icons, one for the shortcut I made and one for the actually running program (non portable exe).
Not to even mention file association if I want to make it the default browser. Which is, I guess, Issue 4.
So in summary.
Portability is completely and massively broken on Iron.