I hope you meant to say restain the siding and not paint. Paint will peel. If you have no peeling and the color has simply faded, then you are looking for a new stain color. Duckback produces a very good stain.

OMG do not place a black roof on this home. First, have it washed and examined. When you live in an area with trees it's important to keep this mildew to a minimum because it kills a roof quicker. A roof should last about 20 years and if the shingle edges are not curled and the nails are not popping out, then this roof is still good. Metal roofs are $$$ but do last forever. You have a contemporary home of no particular style. It's not MCM because it was likely built in the '80s or '90s. It would be most likely called Shed because of the roof. I think the trim, siding, and windows are painted just a bit too dark and should not be such a sharp contrast to the brick. Once the roof is cleaned you could consider staining/painting the siding a lighter hue.

It's a great house. These 'shed' houses look best to me monochromatic- I would paint everything (except the stone) Sherwin Williams Black Fox or Urbane Bronze. When you can afford it the deck handrails could use updating ( I would replace some sections with stadium stairs and others with glass). Otherwise punch up the landscaping a bit and you are good to go. The pine next to the house is so pretty, I don't love the cedar between the garage and the entrance, it looks like it is in the way?

Is there paint on it now? If so, you cant put stain on over the top. You will have to repaint it, or use a solid color stain (the grain wont show through, like regular semi transparent stain). I would try to do a color very close to actual cedar siding color.