SFGate

jessbvg I also don't mind painting front door :) it's maroon with yellow trim. No, I didn't choose the colors!

The Color People I assume you are in the South if your house is cypress. If you want a uniform look paint is your best solution. A solid stain is basically just cheap paint with less than half the mil thickness and will get splotchy from the UV very quickly. Your semi transparent stain is doing this now as you can see up on the dormers. Solid stain only looks worse. You can see this effect also in the third photo

Lightening the porch is a great idea because it will make the house feel much more welcoming. A light porch will step away from the wall of the house and make the area of the porch feel larger and more commodious- like a great place to gather and have a julep.

One solution to going gray is using a product from Cabot called bleaching stain. It is grayish and will over a period of six months or so help bleach the wood to more of a natural weathered gray. It will still remain brownish in tone because you can't remove the current stain but it will allow the naturalness of the cypress to remain. But this is good as it will go with the green roof better than a full gray would. It will look more like the middle photo although I would not use dark brown trim.

jessbvg Thank you for the advice! You are correct, house in is AL.
I am definitely going to look into the stain you mentioned in up hopes it will be a nice happy medium.
What suggestion would you have for porch ceiling paint color and paint for doors?