While it may seem daunting at first, beginning with a clean slate allows you to establish clear expectations and build a strong landlord-tenant relationship from the outset.

You'll likely want someone that can handle A to Z with marketing, pricing, cleaning, maintanence, decor, websites, reviews etc.

Who makes sure it’s clean (your regular cleaner?)

Other than that it's a pretty clean package. 200k down, 720+, 60> ltv owner occupied.  

What if a tenant fails to pay rent, leaves $2,000 in cleaning and repairs, and it takes another month to rent?

At that time I will get the house cleaned up and list it on the market and when it sells I've agreed to get reimbursed my costs for reinstatement plus any other costs plus a fee for my efforts.

Any investors needing any assistance cleaning or restore.

In fact, your feeling overwhelmed is because you don't know how to solve the issues that concern you YET. 

Clean, brightly lit, clutter-free, modern luxury. 

Which results in more wear and tear and cleaning.