Wish I could be more help on the Gag Factory. I just kept trying until I got it "right." You have jumped ONTO the roof to take care of business up there, right? Including the paint under your feet when you're standing up there? I think that was the last bit of it I got.
The clock can be beaten with paint. I'm guessing it's trickier than thinner. You have to paint one arm until it completely turns blue and seizes up, then hit the other one. If you take too long to paint the second arm, the first one will revert to normal, so I painted both of them alternately until they were both close to turning. After that, the hands provide you with a bridge over the thinner and you can paint the clock face.