I realize I opened a wide spectrum for discussion. 

As I look across the US, I'm seeing that different STR markets are in different stages of maturity, and am curious which strategies investors are using to target them.On one end of the spectrum you have mature vacation rental markets that have stood the test of time (long before Airbnb and VRBO existed). 

On opposite ends of the spectrum, I have a property with cheap dues ($25/mo).  

Of course this is well intentioned but a little ambiguous with our interests being on total opposite ends of the spectrum. 

Have had several "consultations" with ADU specialists and have heard a wild spectrum of numbers range up to 25k just to get permits.

Have had several "consultations" with ADU specialists and have heard a wild spectrum of numbers range up to 25k just to get permits.

This is just to say I try to look at a broad spectrum of data and opinions, sometimes conflicting - like Ivy Zelman - to try and understand. 

She has two young children, one of which is on the autism spectrum, so moving twice would be difficult for them.I'd like to help out and purchase a place that they like, and then once they close on their sale, have them purchase the home from me.Market where they want to buy is super hot, so a contingent offer won't work.

But you keep on dredging up these sob-story examples of marginally competent self-managing landlords who are, surprise-surprise, being run out of business by COVID adversity.If you're going to self-manage down at the lower end of the property spectrum, you had better be made of sterner stuff than this lady.

Listing noted both units are rented month to month at $1,350/mo each, which was on the lower end of the market.What I liked: (i) Location (nice B+ suburban area, close to the Villages and Orlando, 65%-35% own to rent ratio; that particular pocket had low to no crime and no registered sex offenders vs. other parts of town), (ii) Product type (3B/2B duplex with a garage, which is rare to find and is ideal for both a small family or a single professional with or without roommates; most duplexes on the market have no garage at all and are 1B/1B, 2B/1B, or 2B/2B), (iii) Age (2006, i.e. while it was on the higher end of my age spectrum it was less than 20 yrs old), and (iv) Upside potential - opportunity to bring rents closer to market post close (tenants were on month to month leases) and forced appreciation by performing minor refresh with some deferred maintenance expected due to age (roof, HVAC, heater).