It is not uncommon for auctions like this one to get rescheduled multiple times before ever actually making it to the courthouse steps. 

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

@Dona CardenasI personally think actually owning physical real estate is the best way to go especially using leverage.  

Is she paying a property manager?

Probably starting out small Jaycee - SF or maybe some smaller duplex type properties.

It gets tricky because wind can be argued as the cause for almost anything, besides water.Is there a way to complete some preventative measures like cutting trees back around the property...? 

Find a better property manager.

.⚠ Unstable Employment – They may have lost the job or never actually started, making verification impossible.⚠ Other Issues – They could be hiding something (evictions, unpaid rent history, or other financial instability).What You Can Do:✔ Ask for the official employment verification letter – Many HR departments provide standard verification letters upon request.✔ Verify pay stubs – Cross-check them with bank statements to confirm deposits match.✔ Call the employer directly – If HR is off-limits, ask for a manager’s contact instead.✔ Stick to a Consistent Screening Process – Fair Housing laws require uniform screening criteria, so making an exception for one applicant could lead to discrimination claims.

Recommend that you speak to someone that actually does STR or is a professional. 

Is a DSCR loan refer to doing that for 1-4 unit properties?