Sometimes these are the best way to learn.You can try - meetup.com or eventbrite.comGood Luck 

Perhaps I'll try to acquire around 3 properties in cash deals that need fixing up, rent them out, and then hold onto them... forever?

Trying to read between the lines it sounds like you have a regular owner occupied homeowners policy in place on a rental property. 

Guess my question is this — where will these employees be living/trying to live?

I had one I tried to get resolved years ago.

*As a side note, I think maybe it would be fun also to try and identify where new technology or machine-learning driven approaches could increase efficiency in the spaceAs for my financial situation, personally, I have around 50k saved but 20k of it is tied up in assets I don't want to pay capital gains tax on.

I tried using the biggerpockets rental calculator this morning and the cashflow was negative, but I may have been too conservative with the numbers.

One thing I’m trying to figure out is how to find good locations where property prices are relatively low, but rental demand is high.How do you identify these areas?

You want this to be your backup plan if things take longer than anticipated, you do not want to dip into personal credit cards so i would use a heloc to help with down payment but try to keep a nice available balance on a heloc as your insurance policy. 

It is going to be an uphill battle trying to prove material participation with a property manager.