Is it asking too much when 3 or 4 roommates want to split the rent for this requirement?

If the neighborhood schools are not the best than you are targeting young families, roommates or couples.

Get a room mate for $500-$600  and you practically live for free.  

Get roommates you like and live there so you can keep an eye on your investment.

These houses are not VR's, they are places to stay for refinery contractors doing short term jobs.My logic is that the more people I can put into a place the longer it will be rented out.  1 or 2 guys might be transferred to a Texas or Louisiana refinery, the other guys stay in the house and find new room mates. 

I know the popular opinion is that special assessments can wipe out cash flow, not all associations allow renters, association policies can suddenly change, but I successfully house-hack through roommates in my Ukrainian Village condo right now (I'm 25 so for now it feels weird NOT to have roommates), and for my first true investment property I want to stay close to home (no more than 20 minute drive/public transit). 

My roommate, (who i plan on partnering with) says that our first deal should be a fix and flip because we're looking to achieve a goal of around Twenty Thousand Dollars fast off a flip.

You are managing roommates or AirBNB guests.

A condo with 2 or 3 brs can be a nice first time purchase in the area so you can get a roommate or two to help alleviate the cost of the mortgage.

Also, I'd find a lawyer that is well versed in the REI world, like I mentioned I don't have any experience with room rentals but since you will be getting a roommate in your own home I'd make sure you have a clear lease with even clearer boundaries while still adhering to the MA tenant laws that apply.