Some tasks can be automated to a degree, but you still need a real person for understanding markets, negotiating, answering questions, etc.

People generally look for the one thing to fix this problem instead of creating smaller changes across the broad context and shifting the overall perspective associated with addressing the issue.  

Do you associate with a cleaning company or some one off cleaners in the area.

Yes, there are automations that can help you, but no automation takes care of a brand new bee hive under the front deck, or the air conditioner that broke down when it was 95 degrees out. 

Back in 1960 if you had a college degree, average starting salary was $6000.

The main property has 270 degree lake views and is located about 40 min from one of the most moved to places in the country.

They steal stupid stuff like people's flip flops. they party late into the night on weekdays. they behave as if residents are there solely to facilitate their good time and buttonhole them for information and directions when they're out walking their pets. they tailgate at the beach access because the hosts are too cheap to pay the association dues. they trespass on resident's property to fish and sightsee then become belligerent when asked to leave. etc etc etc.It really does degrade the character of the neighborhood and the experience of living here during the high season.  

If you do decide to do a flip, I would visit your local REIA (real estate investor association) and look for someone there. 

Buyer covers EMD and all other expenses associated with the deal, title, because you are no longer the person purchasing the property.This is the simple version.

If they didn't associate it with these issues, then it is probably a "nice to have".