A true free market doesn't exist as far as I know.

- Has anyone had an issue with banks or insurance as far as the public record stating one thing and the actual use another?

And as far as people telling you about "appreciation", remind them you are in MI, by the way. 

The desire to connect with others who share similar experiences is so important, and I commend you for seeking out that community.

Feel free to DM and we can see if you’d be a good fit the market I work and if not, at least I can give you a few pointers as far as STR fundamentals and a couple resources for cost segregation.

As far as I can tell all it does is cheapens your fees if you get enough bookings through VRBO.

This is so fundamentally wrong, but for different reasons too.

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That's my personal style; not threatening or hostile, but more of a " hey, lets see if we can get this back on track, otherwise you'll probably have to move back in with your Mom...".If your money is so tight as the landlord that you are maximally stressed over rent coming a few days late, you need to work that out on your end and not create a problem where there really isn't one. 

The best we can do is give you the tools to help analyze deals faster, from there real estate is so subjective and often "one mans trash is another mans treasure" so it's really about getting your brain used to looking at these numbers.