I'm just starting out with a STR and I'm in the process of vetting companies for tax strategy and asset protection. 

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.

Do you need to refinance quickly to avoid a balloon payment or other financial pressure?

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.

Seller of said property is not willing to do terms.I go forth into the MLS or elsewhere and find a seller on any type of property willing to do the terms I want AND is ok with me selling their property and substitute the collateral with another real estate asset of same/more value.

If you truly enjoy property management, it might be for you, regardless of financial consideration.If evaluating the question purely from a financial standpoint, it comes down to the value of your time. 

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

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. 

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

@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?