I know its expensive but you will be well protected :)Or you save a lot of money and be better protected by doing this consistently and well:-carry appropriate types and amounts of insurance-sign contracts with indemnification provisions- obtain all necessary licenses and permits to operate your business-ensure all vendors/contractors are licensed and insured and list you as additional insured-sign well drafted and fair leases and be a responsive landlord -be an active owner or hire an active PM  who avoids or at worse timely eliminates premises liability exposure The strategies you often read about are sold by alarmist asset protection companies who fail to disclose how impractical they are.

To echo all of the above tips, the key ingredients to all of this is consistency. 

Even after seven weeks of troubleshooting with Stessa's support, my accounts aren’t consistently syncing.

This team consists of an Investor Focused Agent, Lender, Contractor, and PM.Read this article on the "core 4".

These are all issues you will consistently need to be able to solve anywhere in the Chicago market though. 

They would be managing 4 to 5 cabins, and I would be setting my daily rates dynamically to maximize occupancy, so this would be a consistently significant workload for the VA(s).

A grading contractor should be consulted for further evaluation and repair.From the attic, some of the fascia boards and the ends of some of the roof sheathing were discolored in a manner consistent with water penetration.

As long as you are consistent and have documentation of changes you shouldn't have anything to worry about.

That inventory is lacking and 3 bedroom homes are consistently being absorbed in less than 30 days without concessions.

Staying consistent and adapting to market changes will help you meet this goal.If you need help with financing or property strategies, feel free to reach out!