@Nick Rutkowski If you have all of the furnishings already I think you can set this up with the help of dedicated cleaners and some automated tools like smart locks and exterior cameras. 300x5 units is an extra $18,000.00 a year passively which may not seem like a lot to some but if you already have all the start up supplies which is the bulk of the upfront costs I say why not.

Wherever you can automate things and cut out wasted time or inefficiencies, do that.

Homepath uses an automated system.  

Automation, etc. may propel the global economy to new heights, but social strife due to inequality (who benefits from the changes) may also tear things apart. 

Make the schedule and steps so simple, direct, straightforward, and automated that a 12 year old could easily run your management system. 

I think automation of home building technology (many off-site 3D printing players, some on site automation tech for construction of tract homes) will be a real factor in the next 3 to 10 years that will be the primary/only saving grace to actually make housing more affordable (easiest way to meaningfully decrease build costs).

The manufacturing companies that do have direct employees are almost fully automated and only have about 80 employees at each. 

As people have already mentioned, there are not any reliable automated tools for posting on craigslist.

Now, I'm not against hard work, but the idea of (at least trying) automating the acquisition process immediately captured my attention.

Setup a automated MLS listing via your Agent (Make sure you have an agent who is ideally an investor and a property manager themselves) BP members and PODcasts has plenty of info on how to and where to get money/deal/contractors and the whole thing.