Does anyone have any experience with using an FHA 203k Loan on a multi and turning it into a house hack in Massachusetts? 

I look forward to reading more of your experiences.  

Others may have personal experience to share.

Share your experience with DSCR's Below 

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?

How has your experience been so far with out-of-state investing?

Nobody ever went broke over a duplex, I know this now,  but I have to admit I had some serious doubts about this when I started 16 years ago, I bought every course I could find, already on CD's, this was post cassette tapes lol, and I paid RichDad Education for a one year coaching program (turned out my coach was a girl in a call center without any actual experience). 

Through my experience, I’ve cultivated a conservative approach that balances opportunity with risk management that I apply to every deal that crosses my desk.

I have no experience with this group but just visited their website. 

i say that not to discourage you, but so that you have a realistic picture of what to expect.as @Travis Timmons alluded to, you need to be in a strong financial position to even think about starting to invest.