, even if that means to barely have cash as a back up. 

The appraisers need pics to back up their lowball appraisals.

As a backup, ask the local realtors you know.

But maybe I can find somebody to partner with here in the Chicago suburbs at least until I can get back up into Wisconsin.

During your due diligence you'll want to back up the financials with one year's utility bills, copies of the service contracts, and a lease-file audit (comparing the leases to the rent roll).  

I self manage our STRs and communicate with guests, but I have a cleaning staff, backup cleaning staff, and a handyman who can typically respond the next day.

Once I was pulling back up to my office and there was a guy just down the street that was stumbling around and fell down in the street.

My other concern about storing it in your desktop would be how do you handle backups??

For exampleA/c condisation drain has a back up.

Furnish all the bedrooms (Craigslist $100-300 per bed with preowned mattress, buy $10-20 mattress cover, $10 lamp, $50 dresser or nightstand) and provide the kitchens with basic supplies (Walmart $20 4 piece set, $10 silverware, maybe some pots or not, can buy 1 multipiece set and split it between your units)Install Schlage Camelot electronic Door Code locks on the door ($100 Amazon-no lockouts) or a lockbox ($25) with backup keysPost on Nextdoor and Craigslist looking for a “house Mom” / Cleaner who will clean units between guests for $20/turnover.