For your payout, I don't know the full story but Airbnb doesn't cover extra fees including cleaning fees.

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

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.

That will probably be your best bet, to buy a fixer and get it cleaned up and then rent it out.Best wishes and good luck with your endeavors.  

Does anyone have a recommendation for a reliable, quality cleaning company with great communication?

See the fact that mortgage rates are up about 1% from Oct when the fed started to cut the fed funds overnight rate as evidence. 

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

Lots of leg work, calls and emails, but if you can find a few deals that could get you started with enough capital to get into your first deal on your own.

If you have the sellers, the buyers will start reaching out - it likely wont work for some of them and then you can ask what they are looking for and build relationships that way.

The Roi combined for 3 duplexes after repair will have an ROI of 4.47. If I managed the properties myself, I would save about $900/month. Would that be worth it? I'm just thinking about the time it would take me to sh...