Working with a CPA or financial planner can help optimize tax strategies and ensure the best approach for your goals.This post does not create a CPA-Client relationship.

I don't want to name names, but I use a major US financial institution for my banking.

Prioritize your financial stability.

A STR is a completely different animal in my opinion, in that it requires more work and much more compromise, but financially is worth the effort. 

We have a solid system in Quickbooks and want to stay with that for financials.

The borrower's financials play a big part as well.

Communication and setting expectations are key to any smooth financial transaction. 

@Christopher HeidrichRecommend 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?

Regarding financials, the bottomline is the numbers should work.

@Jacob HavlovickBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.