For short term rental booking that is cancelled early, the guest is to leave on the day of cancellation and the host will not get paid for any additional nights.

In addition to the different tracks @Chris Seveney descrubed, there is also good information on creative financing and seller financing (including what to avoid).

Are you prepared to kill the deal if the seller does not give you additional discounts/credits or security deposit credited to you?   

Hold additional % into your CapEx! 

I currently have a homeowners plan with Allstate and plan on asking them if they have something like a short term rental rider plan that I can add in addition to my current plan.

In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.

Unless you suddenly become a stellar STR Host and property (requiring additional spending), why not sell and make some better financial decisions....

If you can add a legal ADU at $25k in the Austin area then you should add it.  

You can increase returns with leverage (that is a mortgage) or with value add (renovations, additions etc).I think cap rates (rents minus expenses divided by purchase price) on commercial and industrial is higher with less work involved, but its more expensive than I can afford--so I know next to nothing about that land.

Cross-Collateralization – A lender may finance the full $160,000 purchase by using your existing properties as additional security, lowering their risk and possibly reducing your down payment. 5.