To maximize the number of transactions you’re involved in you will need to:Be Top of Mind when they think about moving - which requires consistent reminders.Be seen as an Expert – which requires a consistent message and Evidence of Success storiesGain their Trust – which requires communicating integritySo, start out by listing everyone you know in an Excel spreadsheet.

All the best  Again, you can't stick to a consistent schtick Bob.

We just got it online in March and have had pretty consistent rentals, but are doing more direct booking than with Air B&B (through networks). 

I am considering MF solely owned properties first only because of consistent cash flow. 

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).