I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

I was living in Kennedy Town for two months last December.

Hi Devin, Have you ever considered that instead of America needing smaller homes that are more affordable, that America needs more higher paying jobs so that people can live the actual American dream versus having to settle for less and less and less (Has George Carlin pointed out in his classic speech about this). 

Like the others mentioned, either 3.5% down if you intend to live in it.

As I grow I will hire a virtual assistant to take a few more tasks off my plate to allow me to live the same lifestyle. 

I live in a popular vacation town in the mountains of Western North Carolina.

Burlap on the wall, postage stamp rug for a large living room, hodgepodge of items around the house with no real theme.

We live in a world where PR matters to EVERY business out there.

You could start by reaching out to any local corporations that do assisted living in your area and see what they are looking for (location, space specs, etc). 

I am seeing a crackdown on STRs not so much as a result of any hotel lobby, but as a result of regular citizens complaining to their elected officials that they don't like living next to a hotel.Can't really blame them.