Make sure you use the appropriate paint for the wood. Some use the marine paint so it lasts longer in the heat and rain. I would ask the paint store in your area. Take a pic of the shed so he knows what kind of wood it is. If it is that T-111, I have that on my shed. I was going to stencil flowers on mine. I have fake windows, a fake door towards the street, I used 2 old shutters and then some wood pieces to make it look like a door. It needs painted too and I will have to take down the shutters to paint it. The other end is an old large wooden window with shutters on.
In the back, I took shutters and actually built a potting closet I will call it. I used one shutter for the side, and I put
2 shutters together for one door, 2 shutters for another door, and then a shutter for the other side. I used a piece of wood for the roof on a slant and added shingles. Then I added shelves. I put all my pots in it over the winter and tools. It is only a shutter deep, that's why it looks like a closet. The neighbors thought I was very clever. I added an old bicycle with a basket, and planted around the two sides. I want to add a planter box under the fake big window.
Just a suggestion for you to maul over. Have fun painting. Now I might take the fake door down and paint a quilt.