My question today is about painting vinyl siding.

https://www.thespruce.com/how-to-paint-vinyl-siding-4150400

Most people purchase vinyl siding so they will never have to paint. By painting yours, you'll enter the realm of needing to repaint it just as if it were wood or another type of siding. So yes, it would need to be repainted regularly...usually every 6-8 years. Since the vinyl is not very porous it will be more likely to chip and peel than if it were wood. I suggest that you clean your vinyl well (which you'd have to do anyway, to paint) either with a pressure washer and soapy mixture and see if that doesn't "brighten" the look. And maybe you could just "freshen" your current trim for an updated look.

A link attached about painting vinyl siding. Hope it helps

https://www.bobvila.com/articles/how-to-paint-vinyl-siding/

Diane KirsteinJust nowTo paint under the lip of the shingles use a brush. I’ve tried everything including a paint sprayer. Unless you have a professional paint sprayer (expensive!!! The smaller ones get clogged w/ the exterior paint being so thick, more trouble then it’s worth) I used a foam roller & a brush yes it took a little longer but loved the results. Sherwin Williams has a paint that is for Vinyal siding that also works on woods. I painted my house 13 years ago from a blue to a light cream color it took 1 coat & just now I need to do touch ups. It holds great & I have cold harsh winters & HOT summers.

Btw I do wash the house w/ a pressure washer & I spray cleaner on it & it’s fine. BUT if you use a pressure washer DO NOT stand as close as you normally would cause then you are @ risk of removing the paint as you would w/ anything when power washing. I’ve never experienced peeling paint