They love to sell you on the dream of easy money but rarely talk about the times when things don't go according to plan.

@Gregory Schwartz That's an excellent point and one of the downfalls of over complicating your entities.

My costly mistakes came from thinking I knew it all.Begin with house hacking - buy a duplex, live in one unit, rent the other.

I appreciate your time 

Hey Jay - I too am asking why :D My only experience has been with conventional mortgages - I recently purchased my own home with one and since I am a small business owner it was like pulling teeth. 

Are there certain abilities that come with having one? 

this property is zoned for office / medical facility, multi use but has a residential house on it.
would love advice from the community on how to
1. analyze potential
2. source funding
3. evaluate market value of ...

@Kevin Morgan are our apartments scattered site, or are they all clustered in one or two areas? 

Hey, that's a great question and definitely a smart one to ask when you're diving into the details of STR (short-term rental) investments.Let me break this down from both a tax and practical standpoint based on what I’ve seen with clients in similar situations.

Of course, tough to build 50,000 units in one person's back yard, but there will be some people build granny flats, or garage apartments and you may see some office converted to residential.