Maybe be inspired by them next time.As an epilogue to all this, I ended up contacting my parents and telling them that I asked strangers on the internet for advice, and it turns out I really misunderstood depreciation.

It seems to me that despite the near-constant protests to the contrary from certain people in the dark recesses of the internet, the tendency of large countries with powerful militaries is that they do not collapse. 

Be Careful With Referral ServicesMany of the flat fee MLS listing service providers you come across on the internet are actually just middlemen.

See here a couple diagrams to help you in this quest:Asset Protection Decision Diagram - to help assess the need for asset protection, and what to implement : https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-decision-diagramAsset Protection Onion Diagram - what, when and at what cost one should implement in terms of asset protection - https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-onion-diagram-v2

Eventually there's going to be a site that's good for owners, probably a flat fee model, free for users and the savings will destroy VRBO and Airbnb.

Another way are old school syndications (which are basically the same as crowdfunding but not done over the Internet).

We look around and theirs seems to be a complete system with free software access that users can customize and send bills to tenants using emails and/or text messages.

They are free (or at least free up to a certain # of units) and offer  most of the same features  along with very friendly user interfaces for both tenant and landlord.  

$15 - just having them come and go, change lights on and off, make it appear occupied encourages party kids, drug users, and bad guys to go somewhere else.

I use Airbnb.com because for me, this is the most user friendly sight.