Is there an ideal time to apply? Is 100 degree weather too hot to apply this type of paint?

My house hasn’t been painted in at least 12 years. We had it power washed but not a lot of paint came off. The paint that is left is pealing and cracked looking all over the house. We tried scraping the paint but it seemed impossible. Do we need to

I need to paint the trim above a shingled porch roof. I’m looking for pro. hints on how this should be dealt with. I will need to be standing on this to paint. Would you cover the shingles with something (and if so what) or just be prepared to wash