If we remodel the basement we would rent it out as a separate Airbnb.

Use a separate checking account for the property.

i just posted this question on a separate thread and wondering if you might have some insight..i have some money through my 457b contributions, a portion of which are in a roth ira. if the math checks out on a property (perhaps a multifam i can house hack), i think i can do better investing my roth ira into a buy/hold real estate. have you come across scenarios where investors found some loopholes with the least penalties or tax impact on such a strategy?

Our properties: (I have listed what the two properties are, as well as some financial information in this section.)Our goal is to ultimately title the properties under separate LLCs.

I might PM you separately since it sounds like you're super familiar with the area.

I am curious if it is possible to get an FHA loan for a 4 unit deal that is separate properties. 

@Michael Plante no I pay my insurance and taxes separate every year.

The landlord tenant relationship is a business relationship and when you live with your tenants it is much harder to make that separation.

The real problem is getting your tenants to separate what can be recycled, what is real trash and what can be composted.

Emotional Intelligence is pretty good too.