I am just looking for insight from local MA realtors, attorneys or landlords regarding what my typical monthly expenses (if any) will likely be (I don’t mean one-off expenses like roof repairs). 

The typical clients that seek out cost segregation studies include:Real estate companies that buy and sell multiple properties each year.Individuals with a portfolio containing investment properties including apartment buildings, multi-family homes and even single residences.Franchise owners with properties that are similar to one another such as assisted living facilities, storage facilities and golf courses.Business owners of hotels, food facilities, shopping centers, restaurants or manufacturing plants.It depends on the type of property, but generally 15-45% of the building’s costs can be classified into assets with a shorter life.

Without proper planning, house hacking can become a financial strain.DM me for further questions or assistance if needed.

It's also important to be aware of any deed restrictions or covenants that could impact your intended use of the property.A Personal Anecdote:I once assisted a client in Omaha who purchased a Freddie Mac home intending to convert it into a rental property.

Getting seller to do repairs. 

Feel free to connect if you'd like more information on how they can assist you.

ya, offering assistance.   

While showing one of the newly vacated units to a potential renter, he informed me that he was displaced because of the hurricanes, and that FEMA was providing him with assistance for moving, including paying his security deposit, rent, and moving costs.

Let me know how I can assist!

I'm also an investor/lender so I can assist with any questions you might have!