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Hey folks, DIY full noob here. I have a separating baseboard problem (please see the attached photos). My guess is that I need to replace a wall anchor, but how do I figure out its size? Shall I do anything with the hole first? Never dealt with wall anchors, wall drilling or anything like this...

Hey there, I am a computer programmer with a background in mathematics. I used to be mostly into abstract stuff like coding and algorithms, I would spend hours after school in front of my PC creating some application. As you might probably guess, I was not good in DIY'ing. To be honest, I am...