And just replace the damaged wood for about $4 a board.

Get a local architect on board.  

Just chalk up the extra time and money to learning the ropes.

We then let people help out and try their hand at installing a few boards. 

I've also heard and know of at least one example of boarding/rooming houses in the urban core.

I have a wife who is totally on board with this endeavor.

Give the tenant 30 days notice and chalk it up to a learning experience.

Just spot checking the search results there are addresses I know are barely standing, partially burned, or boarded up, that they have categorized as "occupied". 

The main problem is getting the tounge and groove into the long end at an angle but then we are finding it borderline impossible to slide the board or get the tongue and groove into the short end. 

Out of 1000s of claims I have worked I was never prompted to state number of occupants in a risk in any report.I have never worked in Wisconsin..... state boards of insurance adopt different language for their policies.