We bought as a house hack, one unit rented as we lived in and fixed the other.

Scenario 2 is technically not house hacking, right?

I'm a local broker, multifamily investor, and property manager.

Its actually easier than wholesaling houses.

You could do that for 3-5% down.. live in it for a year to meet typical requirements for use… then move into a new house, and ‘voila’ - you bought your second (multi-family) rental for 3-5% down instead of 20-25%.It is entirely possible though that you will face debt to income issues on your first rental if your lender wants to see a year or twos worth of rental history before counting your rental income to offset your debt payments…so beware of that.Otherwise you may have to look at creative financing… maybe bringing in a money person where it was a short term investment for them, like “I’ll give you 8% on your money (versus the 4-5,% you could earn from the bank CD) if you will partner with me on this purchase.”

IRS Publication 527 is a useful guide.If you rent the house out long-term, you’ll depreciate the asset over a 27.5-year period.

For those hoping to do the same as us, here is this link to all the information for the Howard County Rental License (link, scroll down to "Rental Housing License") and the actual License application itself (link). 

I also want to get a house in their current school district (as living with this family member is becoming too difficult).

I manage the rest on my own.

How do agents market upcoming open houses for their properties other than posting to Instagram and setting the open house times on the MLS?