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

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

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

I sold out of Mammoth because I had already captured a lot of appreciation (equity) and I saw the writing on the wall with the fires an insurance premium increases.

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

With my LTR's they are mid tier for the market and in areas that have had consistent appreciation for years (before I bought it and have continued after my purchase).

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.

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).

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!