I have seen some good repaint jobs on siding by pros using air sprayers. If you plan on using a roller and brush, you may be disappointed with the results.
Also, if the house is siding and brick. Keep in mind that over time, the painted siding will begin bleeding over any brick below it. This makes a house look like hell.
If the house is frame with all siding, I would spray it or have it sprayed. If the house is brick and siding, I would replace the siding with vinal.
Remember that once you paint siding, you are creating a high maintenance item that will need to be redone every 5 to 10 years.
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