ZONE 7!!!
Ask tons of questions about whole roof condition, decking condition, truss condition, soffit fascia board condition, how they blend the new shingles with the old etc.
You lucky dog! Your winters will be much milder then mine.
Ok so to start make a list of everything that needs fixing. Then one of what you would like to have in there like storage for shavings and egg gathering.
The door issue could be from one side settling or the other being raised by ground swell over the years.
To check level (without an actual level) take a small white container and mark inside using a sharpie and ruler every 1/4 inch. Fill halfway and set on the floor making notes of where and whether level or not. If unlevel note how far off. A larger diameter tub would be better if you have one. (Very redneck way of getting a rough guess lol)
In your last pic it looks like there is some siding damage. Easy enough as that type of siding is still available at Home Depot.
Your roof...... The leaks are a bit more to deal with. Shingles are not super easy if you have never done them before. Since this would be a repair and not a full roof replacement I think you may want to call a few contractors for estimates.
The best part of that is they will share tons of info without realizing you are actually pumping them for it.
The fascia board that I mentioned is the board you show damaged/missing from the tree growing there.
You are likely going to gain enough information to be able to do the roof yourself. Don't forget tar paper and correct nail types. By the way I don't think your roof decking looks overly bad from the side I see.
Adding a chicken door under the window will not compromise any structural integrity. You can put the door or windows anywhere without structure risk so long as you do not cut a wall stud. Wall studs CAN be cut but would require a more complicated process.
As to insulating.... Your zone won't need it. It allows mice and rats to make happy homes in the walls too. I recommend not insulating.
To add a dividing wall..... You will need to do some framing and build or buy a door. That of course can be addressed once the structure is repaired.
Yes you will need tools and safety equipment. Safety glasses are cheap compared to an eye injury. Good gloves are a must too. Saw horses, a jig saw, a circular saw, drill, etc may seem costly but doing this repair and set up may have you building things like chicken viewing benches.
Thanks Old hen for calling me in on this one. You know I love projects!
You'd take the whole door off, remove the latch hardware, and trim some(1/4-1/2"?) off one edge where the two doors meet.
