I reply one by one
1) If you are already doing so, then it is okay, but start from next week, you are no required to put it on comment section, and I think you know how to upload the image at here and select add new image then you can upload already.
2) If you don't get my point, then I explain to you again, let say Level 3366, if you check version page , it has three version of Windows 10 App right, so for my style, I named the level board as shown below
Level 3366 Reality.png (1st Windows 10 Version/Original Version)
Level 3366 Reality-0.png (2nd Windows 10 Version)
Level 3366 Reality-1.png (3rd Windows 10 Version)
Level 3366 Reality-2.png (4th Windows 10 Version/ 1st Version in HTML5/Mobile) - current version
So you need to name the updated image file name called Level 3366 Reality-2.png.
I just want let you know this and you can try it out.
3) Actually, you can go here to upload more images in 1 go, so you no need to press so many time button.
I hope you can understand because actually there are no much people to do editing and I also no try to monopolise this wiki too. Sometimes I also get too tired in this wiki and consume much time to edit this wiki. I also need some time for my other stuff including rest and sleep too.