Previous Homeowner horror story

So, long story short, the previous homeowner added a 3 season room onto this 1905 era home. I purchased it two years ago. Since I’ve been the owner I soon realized there was a problem. The 3 season room should have been properly attached to the house, and now it’s my problem. We get roughly 350 inches of snow where I live and with the snow, and all the rain we get its turned the exterior wall of the house to mush. Currently, the exterior wall is fixed. Had to replace everything from the sill plate up. But my question is, How can I reshape the roof to defer the water elsewhere. And no, a gutter system will not work. Attached are pictures of my dilemma.

Remove the sidewall shingles, install a large cricket, install lap siding. I won’t even touch a reroof with sidewall shingles unless the customer allows us to replace them and install ledger board-z bar detail.

I’m not quite sure where you are referring to when you said install the large cricket. I wish someone could draw a half ass sketch so I know what they are talking about. By the way, I know what a cricket is, just don’t know exactly the position you are talking about putting it.

How much lower is the ridge of the gable from the windowsill? Is there a gap between the gable eave and the siding? How many square is draining from the upper eave and valley? Is the ceiling vaulted under the lower gable?

This is a bad drawing/example. But, is this what you’re talking about?

I will get all the measurements for you tomorrow. Thank you for taking the time to actually look into this and ask questions!

Hopefully you can watch this video because it has lots of pictures and details. Need some roofing advice! #roofinghelp #shittycontractor #sofucked #summerproject #mybrainhurts #fuckthis #shouldntbemyproblem

Awesome design! A shed roof would solve the problem.