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They could make legal arguments about hardship and/or off-sets for non-compliance by landlord, but this would require posting rent or coming even with rent.

You can buy my book, the book from Brandon in the BP bookstore, or Every Landlord's Legal Guide by NOLO. 

Most of the PM work is done on the first 3 months of the management, then we can recoup our expenses. 2. this Is legally required.

Additionally, regarding the legal structure, an LLC seems to be the most suitable option for our situation.

Once you know what is legal (seeing other listings in a particular area does not count as people do it in illegal areas all the time). 

I won't be able to make the cottage legal rental without living in the primary home myself.

A legal duplex will have everything separate.  

I would NEVER Ever use OBIE INSURANCE  --Not honest in their dealings and do not expect refunds on cancellations  I am of the opinion that they are legal scammers Just be careful

@Alvin Sylvain I agree the emotional support animals are B.S. but they are legal and we have to abide by the law.If the animal is an ESA, you are allowed to ask if the person is disabled and what service the animal provides.