In this case, the second bedroom isn't necessary, but does get used as an office for the person working from home.

so, for each individual person, it's more or less doable.if it's going to take you years to save up a down payment, can you increase your income and/or cut your expenses?

It creates a new tax filing, payroll requirements, payroll filings, full books.

Same facts, except that John only has 3 days of personal use in the year. 

Even if your approval goes through without an attorney an appeal can be filed years later after your construction is completed challenging the zoning change (this is the case at least in Philadelphia). 

BUt why cant i get a lien when the person clearly agreed to pay back in a contract and he failed to pay? 

How do you file a judgement against a tenant for damages beyond the security deposit?

I know that much of it is based on personal risk tolerance but any advice would be greatly appreciated. 

So now it hits a rich and famous person.

I used a HML for some and he did for others, only in that person's name.