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). 

For a partnership where you're providing all labor and the broker is funding the deal, a fair split typically ranges from 30-50% for you and 50-70% for the broker, depending on the value and complexity of your labor versus the financial risk they're taking.

I need something simple that I could utilize today.Thanks you will not be able to get something today. in order to pull credit typically you must have a background check done on you and the company will also come visit your office and confirm you have specific security policies and procedures in place. 

For costs, you’ll typically need to budget for title insurance (usually around 0.5%-1% of the purchase price), attorney fees (varies but can range from $500-$2,000 depending on the complexity), and closing costs (might include recording fees, escrow fees, and other admin costs—generally $500-$2,000).

Those groups typically research and know what to expect, which make them “easy” to host. 

Typically they want good credit score, landlord experience, and 20% down.You can get ones that will either use current rents OR market rents.

Typically speaking 20% down (80% LTV) is the bare minimum that commercial lending requires.  10% down is unheard of unless you are getting a great deal and negotiate some small seller financing in second position or getting an SBA Loan for acquisition where your business will occupy over 51% of. 

Since you're currently using the property as your primary residence, the cost of improvements made before it's placed into service as a rental wouldn’t typically be immediately deductible.

Hi @Tim Holt I think in general house hacking is usually a good move because it gets you off the sidelines and into the game with the most favorable financing possible (30 year fixed).There's a lot of value in getting started today vs waiting some undefined number of years until conditions are better, which could be a long time from now, because real estate is a business and the sooner you start actually learning about that business, the better.With all that said, I always recommend that people analyze any potential house hack as a pure investment that they aren't going to live in, because someday they may want to move out and you should know up front (before you commit) whether you're going to be able to do that, or whether you're overpaying and will be stuck in the property unable to move out because it'll be cash flow negative if you do.So you had it exactly right when you wrote, "the property would need to cash flow when I move out and rent out all units."

@Teri Feeney Styers the slow flip method that I think he is referring to is the one coined by Scott Jelinek which is buying a livable property using private money on a short term (typical 60 month--like a car) and immediately marking it up 2-4 times and selling it on a 30 year term using a land contract.