Obviously no roofing contractor would guarantee patching nail holes, just curious if anyone has tried it? 

But the tiles in the OP's pictures are at the wrong height for the chair rail effect, and one one wall is too high, so would need partial demo and plaster patch anyway.  

Patching those holes should not be all that difficult.Drywall is really cheap and so are all of the other materials need to re-sheet a small space. 

If you are looking for more hard money loans, then some of them that specialize are Patch of Land and Peer Street.

@Diane Trotter  since you admit not being the least bit knowledgeable on subdividing. your chance of getting one of the crowdfunding sites  ( Realty shares , Realty mogul, patch of land) to sponsor you or this project is remote at best ..

I've had to replace patches of wood on them three times in the past 12 years and I'm hoping to make my house my first investment property.

While we did buy a number of low priced houses in the Oil Patch, expecting them not to go up, they did double. 

We call a roofer, who gave us a quote of $900 and said he'll come out and patch the roof in two weeks.

When you were GC at Patch of Land, you were the most informative and helpful resource out of all legal and nonlegal resources in all of the 100+ crowdfunding sites.

We can't simply build houses over every non-developed patch of land for so many reasons, not the least of which is, what would we eat??