Today we have 540 units in a few states and things are not without challenges. 

Sounds like this could possibly be a Schedule C activity so keep self employment tax in mind.

Seeking insight from the community on converting a STR (primarily Airbnb) to long-term rental.

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

Cameron - welcome to BP! 

As of today, the house rents for $3,400 per month and my PITI is $2,500 per month.

@Chase AlexanderRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

It doesn't necessarily hurt resale here although you have to know that you're going to be required to carry flood insurance which obviously can skew some numbers.

Mine is 16, and it's like talking to a brick wall.