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I think what you are referring to when you say raspbian is the LXDE GUI (which was removed starting with version 2.4 to trim unnecessary bloatware.) As far as I understand it retropie is still built on raspbian but just lacks the GUI.
Starting with a fresh 2.5 image, to get the GUI back:
Sudo apt-get install lxde
Reboot
Then you should be able to open like you used to with startx.
PS. The reason 2.3 won’t boot on your cards isn’t an issue with your cards. The 2.3 image isn’t optimised for the newer processor of the model 2 raspberry pi. It works fine on the raspberry pi B+.
PPS. I would also look into using winscp if you like the whole windows type looking through folders thing. I used to use the GUI but I’ve replaced it with learning the terminal and occasionally utilising winscp.