@Jaysen Medhurst this is very much a stereotypical "Main Street America" location. 

I highly doubt your friend would be amenable to a blanket perpetual easement on the property for a billboard, but I have seen it happen.

I'm not opposed to efficient urban housing, I just don't want to get rich perpetuating a slum.

Part of the problem is that there is no blanket standard across the board and the only one (blanket standard) that DOES exist across the board is so vague that it typically prompts emotionally discussion across the board because of those who are inexperienced in this aspect of the quality of life for the disabled typically stereotype the legitimate disabled community with the fakers that are out there. 

1 yr, 5 yrs, in perpetuity?

1) You want to get a specific easement that only encompasses the existing equipment2) Longest term easement (perpetual) for the most amount of money.3) Future landlord will receive a % of any future revenue these companies bring4) Make sure your agreement has some type of relocation language.

My background and upbringing is true to form for the stereotypical Wisconsinite: dairy farming.

As a bankruptcy lawyer, I find your post inaccurate and only perpetuates myths about bankruptcy. 

That does not mean they are bad people and stereotyping that they will all fail as renters and cost an investor money or headaches is wrong as well (not that anyone has done that - just pointing it out).  

Or it could be the start of a reversal since California is perpetually in a boom and bust cycle.But look at the worst performers.