In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

I just did one for like 28k, was a little short on a closing cash purchase. 

Start by analyzing cash flow and market demand for each property to decide which one to rent out.

There is currently not a mortgage on the property, but due to the s-corp ownership, refinancing is not going as easily as I'd hoped.

I would recommend finding a real estate cpa even for one property.

If the property were owner-occupied, would I only receive credit for one rental unit's income, while the non-conforming basement income wouldn't count?

One of the properties is a three bedroom with no garage that the tenants pay on time but require more of my time than the others .

Quote from @Louis Hamilton: The property is worth around 800,000 and has no mortgage on it.

At least a third of them are Class D.DM us if you'd like more info on which Metro Detroit Cities & Neighborhoods are what Class:)

Looked on zillow for several weeks.