How to Repaint an Exterior Structure

As times goes on, exterior paint fades. This is just reality. When that dreaded time does finally come around, here’s what to do.
Depending on what condition your walls and siding are in, the need for scraping and cleaning will vary. Light peeling is easy to scrape (be prepared for paint scrapings to be everywhere) and sand for a nice finish, while real bad paint or damaged wood could require pressure-washing and adhesive/filler. The importance of this first step is crucial for a paint-friendly foundation; a new coat of paint will only hold to clean original paint or fresh primer.
After your siding is touched up and cleaned, it is time for probably the most important part of the prep-work; masking. This task involves multiple kinds of tape (white tape is stronger but should be removed by the end of the day, blue tape can be left for multiple days at a time), paper (typically for the snug spaces a tarp can’t close up), plastic (for windows and small, fragile bushes) and big tarps for wherever. Mask off everything you don’t want primer or paint on (if you have to put tape on areas that need to be primed, go ahead and carefully prime those specific areas first). This process can get tedious after a while; just remember, outside of the actual paint, the quality of your entire job rests on the precision of your masking. The few places you can be a little sloppy are on the “out-of-sight” areas around your roof (on top of chimneys, deep inside over-hangs etc.). Spend time on quality masking, better to be over-impressed than under-whelmed at the finale.
Now it’s time to get messy. You will likely need at least one coat of primer (most often latex primer works fine, but if your siding is really butchered, a thick coat of oil-based primer may be necessary). If you have rust or mold in areas (which is likely), you should use KILZ primer; this product kills mold and covers rust all together in one swoop. As long as your siding surface is clean, only the bare wood should need fresh primer. Just make sure all areas you want to paint are covered by some kind of base coat.
Assuming you’ve already decided on paint colors, the next decision is whether to use a sprayer or hand-paint your structure. There are only a couple factors that influence this decision; structure size and over-spray risk. If you have a huge building to paint and don’t want to spend a month painting it, using a sprayer will be the obvious choice. Things become complicated if your building is surrounded by things that need to stay “over-spray free.” Do not under-estimate the range over-spray can travel; even the slightest breeze will carry paint places you will regret. You may have to resort to hand-painting if this is the case.
After a quality coat or two is on your exterior, don’t be too quick to rip off all that masking. Not only may you still have trim or facia board to paint, but there may also be wet paint on the masking that could find its way onto the wrong places; and believe me, you do not want that problem.
Once you are sure there is no more necessary painting and all applied paint is dry, go ahead and pull the masking off and unveil the new look of your structure. You will be very excited once all the paint is on and all masking is pulled. The instant gratification of a newly painted building is very fulfilling.

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