18 year old house previously stained a dark brown. Many sections of varying lengths have been added as replacements for dried out or rotted planks. The replacements are light in color. We want to restain the entire house in a uniform color. Our contractor wants to use a semi transparent

Using the same colors–greenish/gray siding, tan trim, burgundy under the eaves. Which do I paint first? Do I have to tape off to cut in? That would take forever, and I am doing this by myself since hubby has broken leg. thanks 🙂