The roof is leaking

Since you need three quotes, don’t wait for that friend of a friend to come next week. Get a couple right away and then you’ll know what you’re dealing with.
 

Sorry to hear this. This is bad news for you and it gonna cost you BIG Bucks. I have been a home owner all my adult life so I can see all the work involved here. You have to have it fixed because a leak is always bad news. It will only get worse and it will never stop by itself. Sorry to be the bearer of bad news but that is how it is with roofs and most leaks. If you wait too long then your joists will start to rot and you probably heard about the price of lumber these pandemic days! It's not good news! These days I live in a nice new apartment and problems like this don't exist around here. With home ownership there are plenty of "surprises:" leaky roofs, water tank leaks, foundation cracks, home invasions, doors not shutting/opening correctly, etc. Been there, done that and don't wanna go back there ever again. Sorry to hear about your troubles! Best of luck.
 
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From the outside, the roof looks okay in the problem area. I just wonder if the rain isn't getting in somewhere above the eave and running down underneath the shingles and pooling along the edge.
I like you, Deb, and have always got along well with you, and I mean no disrespect to you with what I am about to say, but if there's one thing I have learned about you and your home, you're not (at all) serious or interested in seeing it repaired.

You have had nothing but quality advice cast your way in relation to your house woes over the years, and aside from failing to acknowledge those with a thanks who so kindly took the time to drop-by your started house threads and voice their take on the matters, your house continues to fall apart and spiral further into disrepair and catastrophic decay, and all I see is a homeowner that continues to pooh-pooh the fact that extensive work needs to be done to her home, making up excuses as to why you haven't been able to hire the professional tradespeople you need to rectify your situation.
 

I'd probably move if I could find the right house - 900 to 1200 sq ft. one story with attached garage. Trouble is - there's none with that criteria in the whole county. I looked on Zillow, realtor.com, redfin and trulia.
Talk to a highly recommended realtor (not the one you’ve been using) and who is listing and selling lots. Tell him/her that you are a serious purchaser and exactly what you want. Up what you’re willing to pay - prices have skyrocketed. If a realtor knows the client is serious, you’ll get the first call on new listings.

Once you get a new place talk to the landlord next door and see if they’re interested in buying. Investors often like larger parcel of adjoining land.

Other option, rent an apartment until you get things straightened out. It might be the best decision.
 
I'd probably move if I could find the right house - 900 to 1200 sq ft. one story with attached garage. Trouble is - there's none with that criteria in the whole county. I looked on Zillow, realtor.com, redfin and trulia.
Oh, please. I’ll sell you my home 1350 sq feet, one level, finished easy care yard, but, you know, it needs a new roof. 😂😂😂
 
From the outside, the roof looks okay in the problem area. I just wonder if the rain isn't getting in somewhere above the eave and running down underneath the shingles and pooling along the edge.
The damage in the photo could be old and unrelated but I doubt it.

Next time it rains feel the roof rafters on either side of the area and above it to see if they are wet. The water could be traveling from the flashing around the old chimney at the peak of the roof.

In the photo, it looks like the existing rafter tails have been repaired/replaced with lumber scabbed on to strengthen them.
 
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