Anyone have practical experience with this that we can discuss further?

It can also be probably fight in court if this is a monopolistic practice if you think about it but who will want to fight it :D.  

He ended up finding an eight-plex in a growing neighborhood that’s now practically printing rent checks for him.

I found out in my jurisdiction that medium-term rentals are classified as long-term rentals and therefore have different laws.

My Brother in law has a company that does this and hand full of realtors have him on speed dial 90% is pipe burst done in a few hours 7 to 8k per..

Pre-approval for loans is essential, as is learning landlord-tenant laws to manage effectively.

That said I am unsure of the laws in your state. 

Preliminary experience stemming from construction as a young adult to gaining my degree in law.

Please note that I have 25 years of experience renting out apartments and houses in three other states, but I’ve never done so in MA, so I don’t have experience with local MA laws or vendor expenses. 

Since we are both in Chicago, I would highly advise checking into the landlording laws here.