There is risk with this approach that the tenant can have short residence or leave in Nov to January.  

My goal is to build a data-driven tool that provides actionable insights into which neighborhoods and property types are in the highest demand, based on metrics like:Time on market: How quickly rentals are being leased.Property characteristics: Bedrooms, bathrooms, size, and amenities.Pricing trends: Rental rates relative to market demand and property features.Visual quality: Leveraging property photos to analyze the style and condition of rentals that perform well.The tool will allow users to:Pinpoint areas with the fastest rental turnovers.Understand what types of properties (size, price range, features) rent the quickest.Gain deeper insights into property presentation and amenities that correlate with high demand.Thank you in advance for your feedback.

Once you have enough properties to support your life style, what is the point of acquiring more?

Your life style has lead you to this situation and you must change your lifestyle in order to be successful with real estate. 

With a teaching and leadership backgroud, I have an interest to help others write their programs or review their presentations to address every learning style.

Look at SCI, we had a lot rent increase in Nov. 2017, SCI came in an purchased it in Dec. 2017 and increased the rent again.

I'd recommend interviewing multiple PM's and seeing which one fits your style and expectations.

Both units are approximately 400 sqft, "yurt-style" cabins with large decks.

It might be that this couple that owns the house is just getting their feet wet with having someone else managing the property and they want to get comfortable with your management style as being what they want.

It was a 1962, ranch-style house with blocked galvanized pipes and a busted water heater!