How can I paint the exterior of my house?
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https://www.hgtv.com/design/decorating/design-101/how-to-properly-paint-your-homes-exterior
With paint and a brush?
You have options which range from doing it yourself, to hiring a professional. The best options in my opinion, depend on your particular house, your painting ability, and budget. Feel free to attach images or more details.
Buy the paint and supplies. Get an extension ladder. Start at the back, then sides, then front for prep work, then paint in that same order...the motivaction of finally seeing the front painted will keep you going. See if friends or family will help. Do it anytime but the heat of summer. I've painted my house in the past, hard work but saved tons of $.
The best way would be using a paint sprayer instead of a brush or roller! I would get quotes from a professional on how much it would cost for them to do it!
If you have the patience and time you can do it yourself. Scrape any looks paint off, then use a good exterior paint.
A serious endeavour! Here are some great tips!
https://www.hgtv.com/design/decorating/design-101/how-to-properly-paint-your-homes-exterior
https://www.diynetwork.com/how-to/skills-and-know-how/painting/10-things-you-must-know-when-painting-a-house-exterior-pictures
https://www.thespruce.com/easiest-fastest-way-to-paint-a-house-1821069
https://m.wikihow.com/Paint-a-House
I painted my house when I was very young. Needed to be sand blasted and that part I hired out and did the rest myself. Purchase the correct formula paint for your surface, and buy the absolute best quality paint you can afford. Prep work is key to a long lasting result - do not cut corners. Start on the side or back till you get your groove going. Watch the weather carefully, warm and dry is best, but not hot. Not windy either. Good luck and have fun!
Start with a clean surface. Pressure washing is highly recommended.