Thank you for the kind words, it's been an interesting experience so far. 

For example, the signs of the 2008 housing crash were all over for everyone to see but many investors were blindsided by their "following the herd until the last minute before the party ends" kind of strategy and lost everything as a result.

I had similar thoughts, but with one immediate cheerleader telling the OP to go on podcast I thought I’d just keep my trapshut.

That kind of cashflow is just unrealistic in my neck of the woods. 

They said that kind of project would basically convert the property to an apartment building and requires R6B zoning.

.: :) Yeah, I started off around Reno,NV & Tempe, AZ, but I think the median prices look way higher, so I am beginning to look and research around the areas of Fort Smith, AK,  Cleveland, TN and Ownsboroo, KYOk kind of curious how Owensboro made your list.

It's an area where they generally have not allowed garage enclosures and LOTS of people have done it anyway.There are all kinds of ways the cities find out about houses like this. 

I have clients that have these kinds of arrangements, and while it is easier when an org fills your units, you can lose control of maintenance and cleanliness.

In terms of the second scenario, the upside I see is the option to get a different kind of loan (say, FHA with a lower down payment and other assistance programs for K-12 educators like me) since I'd be getting a new primary residence instead of a second home.

Still, its a great subdivision and there are a lot of investors that know what kind of revenue those cabins should be generating.