I have been working with investors over the last 3 years helping them find good deals on land in desirable locations and then building a new house on it to resell.

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.

Check out Camelback House condos in Scottsdale. 

The first buyer is going to build a house.

So in these historical areas you not only have to work with the city but also the historical societies.I don't think that any construction that the city approves they will later shut down while in progress.

I am about to flip my first house and I'm already learning a lot.

Get an extra job, live off of nothing, and go put 3-5% down on a single family house hack.

Requiring renter's insurance (separate from your property insurance) is also very important since they typically would not have the cash reserves to pay for a major damage such as water damage, ruined floors, fire/smoke damage, and you will be sued by 3rd parties if something happens to them while at the house if they have to go to the ER. 

Most rust belt cities are similar, older housing stock, lower prices, higher risk.  

My partner would not be living in the house.