But he acknowledged that I was already more savvy with using Airbnb’s basic technology than he was; so the upside was only going to be maybe some extra low season bookings via referral from his other properties.

(I have been using this strategy for my part time work for 4+ months now so I am very familiar with it, and have access to technology that simplifies the process).

He has lied to my face repeatedly.

The most overwhelming aspect of this idea is the technology side.

Because it's all lies, BS and internet know-nothings. 

I have never lied to my tenants, but don't always give them the whole picture.  

This time I believe technology has advanced enough plus, the motivation to keep growing and learning is enough to have a better chance of succeeding with online-meetings mainly and  occasional physical meetings.)

Listen to what they tell you and make sure you are as accurate as possible with estimates, carrying costs and rehab prices, etc. numbers do not lie. 

Keep in mind that drug addicts  lie so you are never going to be sure what the real story is. 

Many of the tenants that throw them around fail to read the fine print that they could go to jail for lying on them.