Any guidance is appreciated and I know it's not tax nor financial advice, just your thoughts.

@Ezra Avery you might want to read below to understand Classes of Property/Tenants.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?

I bring sales experience from selling RVs and have always been interested in real estate investing as a way to generate income and eventually achieve time and financial freedom. 

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

@Kaleb JohnsonRecommend 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?

I would agree if we were talking about financial statements, but as I understand it, we are talking about tax basis reports.For tax purposes, one can use a modified cash basis when filing.

Also any tips for automating this as much as possible and how to protect the property financially and property management would be appreciated.I ALMOST understand the rental arbitrage strategy if building a company scaling with say 30 + units and looking for high short term cash flow.  

Greatest financial pitfall when owning a rental property is vacancy time.

Make sure to prepare a professional proposal, highlight your STR track record, and be transparent with your financial projections.

The financial and social extent of this disaster (initially estimated at $50B) is underestimated by at least 5-10X.