You will note there is no mention above about being a good communicator. 

Working with contractors can be extremely difficult as projects get delayed and there is poor communication(red flags were not present before project began).

His communication is poor but he continues to advertise for his several businesses.

Asking travelers to communicate via platforms or services outside of Vrbo before accepting a booking (such as through email or text).

@David Dachtera David, I'm wondering if this is all a big communication issue or if it's a legitimate misunderstanding. 

Which is not uncommon, what is uncommon is the number of inexperienced syndicator’s Who not only lost all the investors money, but some even fail to communicate the status of this indication. .To start, understand the type of deal you want to be in.

Keep them updated to reflect seasonal decor or recent upgrades.Offer High-Impact Amenities: Small touches like a coffee maker, fast WiFi, or a thoughtful welcome gift can transform a stay into a memorable experience.Stay Communicative and Proactive: Prompt, friendly communication makes guests feel valued.

Since September communications have been weak at best though. 

Choosing markets with direct flight access simplifies logistics.After setup, frequent visits are unnecessary if you have a reliable team and good communication.

Do not communicate in any form other than email.How long did it take you to resolve things?