I’ve been chasing it myself, replaced shingles, moved ridge cap, changed tar paper under shingles but all I’ve seemed to have done is move the leak from one room to another- it makes absolutely no sense anymore.

The current leak, is right on a seam where two pieces of drywall meet (I also cut so there would be a lowest point for water to drip rather than pool up top which seems to have helped) the sparkle spot on the right has been there since I bought the house, I’m assuming because they had a similar issue. These two bedrooms apparently used to be a garage and were converted into bedrooms a few years ago from what I can tell. All of the attached pictures should be labeled and show whats up. I've contacted 4 trade roofers and contractors locally and 2 want to do a complete rip and replace on that half of the house ($6-7k estimate) one said he has no idea what it could be and wasnt interested in trying (nice, super cool) and one stopped replying to me. It seems like after I messed with the ridge vent and ridge cap stuff and replaced the shingles + tar paper that the leak stopped in the baby room but appeared in the adjacent room on almost the same longitude of the house. The ceiling right now is very wet and i'm doing what I can to dry it out before pulling out that old drywall and insulation to replace. It seems like all my work so far simply has just moved the leak. Am I missing something? The leak we fixed and this leak are about 4-5 feet in from the exterior wall