The drawbacks are that repairs/modifications are expensive due to the house’s age and that I have to clear everything through a historical society as a result.

I actually advertise on rescue and humane society pages ect for this... 

I'm bad at predicting them and even worse at predicting how society will handle it. 

Most people overlook mobile home parks as an investment vehicle due to negative perceptions about the kinds of people that might live there or what they represent (poor, dirty, untrustworthy, etc).

The riskiest scenario above makes $0 and this brings out a good point about risk and our perception of it. 

You are not in control of their perceptions, you will not be in control of their reactions.

My perception is everything is insurable.

You've paid your debt to society if you've served your time," wrote the bill's sponsor, Councilmember Lisa Herbold, in an August 11 blog post.

You will be surprised at how much inspectors and city officials want to be acknowledged and not simply seen as the bad guy....in most cases they are not the bad guy....but that is sometimes the perception.  

The nefarious connotation you imply simply isn't mainstream.I'm as big a critic of misused language as anyone, but in this case, I think your understanding of the term "hacking" is out of line with the rest of society's.