Repainting 2nd floor exterior window trim

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Hello everyone, the paint is starting to chip on the 2nd floor exterior window trim of my house and is exposing what looks like really dried out, cracking wood. I'm planning on repainting it myself since it doesn't look too hard. I'll start by scraping off as much of the chipped paint as I can, then sand with 100 grit using an orbital sander, then smooth it out with 220 grit, put a layer of exterior spackle on it, sand again, then finally prime and paint. Does that sound about right? If I'm missing any steps please let me know. What I'm worried about mostly is how much debris is going to be flying around during sanding and how dirty the roof is going to get. What steps can I take to make the cleaning process a lot easier and make working on the roof a lot safer? All advice is much appreciated.
 
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Nov 13, 2018
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Is there any way to take the windows out? Is there a trim strip you could remove? It would be much safer if you could work on the frames in your garage than on your roof. You would also eliminate the worry of cleaning up a mess.
 

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