help!!

I've been having 2 different problems.
1 this is the most aggravating thing is that every so often it completely shuts down and gives me nothing but a white screen, and nothing I can do will let me recover my work. Anybody know how to fix this?

2 This one is not so bad but I'm converting an old hand drawn map but when I try to change the color of certain terrains say wastelands either it will not let me or I missing something any thoughts on how to fix this would also be appreciated.

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