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To me it looks as if you still have some prep to go....hard to see from photos though. Here is what I would do. Start to finish.
1. Wash house with bleach/ detergent. Apply with pump sprayer, rinse low pressure with pressure washer. Let dry.
2. Scrape peeling paint.
3. Sand any high edges flush.
4. Dust off substrates.
5. Prime with a bonding primer like XIM.
6. Finish with 2 coats high quality waterborne paint like Benjamin Moore.
When I paint shingles I use a 4-6 " wizz roller. I can fly with one and end result is always great. Brush trim.
I hope this helps Jim. Any more questions just fire away.
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