I would try to find receipts, at least contact credit card company or bank for checks or CC receipts.

You need to talk with your attorney and tax advisor to determine the best structure for you and your goals.One big positive in LLCs, even though the cost to finance is much higher (more down and higher interest rates), when you get commercial loans, they will no longer be on your credit report.  

The inclusion of additional units could potentially increase my qualification for higher-priced homes, contingent on the rental income they generate. 

It will auto download and categorize all your bank and credit card transactions, print out reports by category or property, and make tax time a breeze. 

@Angie Hensley, until you do something additional the LLC has no authority to sign a lease to rent out the property.

In addition, MANY real estate investors don't focus on equity/property values they make their money on cash-flow, value add, etc.

I would suggest speaking to local banks and credit unions.

Additionally, in your experience, when is it more suitable to hire a contractor versus a handyman?

Any additional tips or things I should consider would be super helpful!

It reflects the average rental income per booked night, including nightly rates and additional fees like cleaning charges, pet fees, etc.