Would I try to strike a deal with the adjacent owner to repair the shared structural members and roof?

It's interesting, do you strike a balance with preserving the foundation/norms/values of those relationships or do you sing about your passion from the mountain tops?

I should add that the house was built around the same time as the one I recently purchased, and all the rehab work that I've been doing on this one will be very similar to what needs to happen in this other house, which strikes me as an advantage.

Think about it:RENT STRIKES.

You have several heavy weights in this thread giving much better advice than I could probably ever hope to.However I have a very simplistic mindset and sometimes look at things different and maybe my thoughts will strike a chord.- Always plan for the S*** Hits the fan scenario- What happens if the owner dies?

That strikes me as a different model than what most buy and holder are doing.

If you are striking out, then you will be forced to transfer into your name.However, you have to work the field first, and see who can work with you as is.

A simplified example, the strike price agreed is $1,000, the expectation of a price increase or market value is 10% annually or the price is expected to be $1,100.00.

If they are already renting from you, I don't see much advantage to you by offering an option.I usually charge a 3% option fee and the strike at appraised value.

Yes.The differences in these two approaches is striking.