Can you help analyze this idea

[Jesse Aaron]

Hey guys, I took a major step (in my mind anyway) and scheduled a couple showings with a realtor to look at potential rental investments. The last showing was the one I was most excited about. A small cottage home on a dead end, wooded street just outside of town with an asking price of 39k (should rent for 600). When we walked in, the realtor noticed water damage on the ceiling that wasn’t there before which means the house will need a roof. This isn’t a surprise as it is an older home but was definitely disappointing since it was advertised as a turnkey purchase. The realtor mentioned the 2 houses further up the road have the same owners (three lots in a trust) one has sold and the other has an offer on it but the realtor doesn’t think the lady will find financing with her credit and income. Could this be an opportunity to make a low offer for the bundle, fix the roof for a rental and offer owner financing for the lady that can’t get financing? I’m new to this so just curious if this is something anyone would consider. She said the other home was going for 52k. Maybe I could offer 70-75 for both using the roof repair as leverage. Any thoughts? Is this too much headache for a newb? I have solid credit and would be comfortable investing 15-18k upfront.