First, make sure the siding is perfectly clean. I don't know if power washing is an option or not, but if not, make sure you really get in there with scrub brushes or the paint won't adhere properly. You would be surprised at how much dirt and dust gets in there, no matter how clean you are. Second, use a tinted primer on the bleached out section, and then use a good quality paint over all of it. There are paint rollers made specifically for textured surfaces. Go to a paint store and ask them if there is anything else that you would need. They will be able to answer all of your questions.

I second the idea of making sure that the wood is changed thoroughly before attempting to paint.

When painting our kitchen's ceiling beams, I found that the oils in the Douglas fir kept seeping through the primer, so I ended up having to redo it with bonding primer, which took much better to the rough-hewn wood. We had to go to a specialty paint store for the bonding primer, as the major home improvement chains don't carry it. Good luck!

My house was modernized by an architect who covered it in cedar. It is dark gray, almost black. The finish is oil-based. It looks fabulous. It might not be as rough as yours, though...

You'll need to go to a real paint store and ask their advice if you want to DIY this. Skip the big box stores.

The local folks will know your area and the elements and the protocols to follow.

You are looking for a store that specializes in paint, so Sherwin Williams, MAB, Benjamin Moore. It looks like Hirschfields is the BM dealer in your area.

As mentioned you'll need to really get the stuff clean and then probably use an oil based, stain blocking primer, folllowed by your top coat.

The pros will make suggestions on paint and number of coats etc.

Exterior stain comes in a lot of different colors/finishes. The benefit of a stain is that it doesn't peel (unlike paint) after a lot of weathering. Eliminating the need to scrape when you need to repaint. Would seriously recommend looking at exterior stain options - you may find it to be easier than painting but yield the same result.

I was just about to say the same thing as @JenPDX

Take a look at solid color stains. They come in many colors and also can be tinted to match most chosen paint colors. I recommend Cabot brand, I have had very good luck with their solid stains (Cordovan and Slate). http://www.cabotstain.com/colors-and-finishes/families/Solids-Colors.html

I suggest first using a NON TOXIC fence/deck cleaner -
http://www.osh.com/eng/product/simple_green_deck_fence_cleaner/6596787?gclid=CMS2zNqexbUCFcdDMgodwGIAsQ

I agree that you should use stain instead of paint for maintenance reasons. The end result will be more natural than paint because the wood texture will remain.

I also agree on using a dark grey color stain. Grey is a color that goes with everything. It is a color that often appears in nature and will make other colors you put in the space POP. It is modern and sophisticated but is subtle enough to not overpower.

There is a type of paint called barn paint, made for rough applications. It is thicker than regular paint, and lasts longer. It is more expensive than regular paint, but will do the job nicely. Several manufacturers make it. Ask around your area.

i second about solid stains. my house is also rough cut cedar. it used to be a dull blue grey and i redid it in a solid stain called indian corn (great for the country setting) and did the trim in a nice warm white. looks amazing.

My friend's brother is a painter, and she had a similar problem when wanting to paint a rough brick exterior to her house. Based on his recommendation to her, you will need a thick fluffy sheepskin roller, and appropriate outdoor paint for the weather conditions in your area.

I now know what direction to go with this. Good cleaning. Primer. Wood stain. Deep pile brushes. And - DARK GRAY -I love it! Makes total sense. I never would have thought of that. What about trim, though - same color? THANKS GUYS!

Any color goes with dark gray. That said, it's tasteful and long-lasting design-wise to do a mid-tone that is similar to the dark tone - something like Dark Gray with Driftwood, or Silver Beech and Pewter.

You could also do a brighter color but similar value tone: Mountain Brush walls with Calgary trim. This is generally harder to pull off, and requires that your house have some solid design element that needs highlighting.