So, when I choose a market for my investors i do some google searches like "Top 10 cities for the BRRR" or "best cities to hold real estate in", "list of cities with the best real estate appreciation over last 5 years.The choice also depends on your capital. 

I have gotten connected with some wholesalers and am on their mailing lists now for off-market properties, so I'll keep an eye on those to see if the right opportunity pops up.

So, coming back to your original question, I think that cash flow should be very low on the list for why one would buy a house hack. 

That is pretty much the minimum list.

I'm a Realtor, so saw it as soon as it was listed and made offer immediately as I was already familiar with the layout, etc.

Unfortunately, communication with the listing agent has been lacking, leaving me uncertain about the progress of the necessary permits and inspections.

My title insurance company didn't pay anything to start because they said the lease with the internet company was not listed at the court house.

I think I should look for a lower list price.

My question is, what stops me from doing the condo conversion and listing the property as BOTH a 2 family investment property AND 2 separate condo's?  

Over the past year or so, I have seen a couple of smaller commercial buildings come on the market that seem to be at tempting price points - 415 N Michigan (listed for $199,000) is a current example.