@Justin Seng I agree with numerous people before me, being that it is a complete preference. 

It's a complete re-positioning.

1)  Pay off your house completely so you would be mortgage free (let’s pretend that’s your mortgage balance)2)  Buy a 250k multi family that brings you 1k per month in cash flow  Close to big city (1hr away )3) buy 10-20 single family  ( which is almost the same as   The same amount of units Multifamily )that cash flow’s $200 per door ,  which would roughly give you $2000- 4000 cash flow per month

My market expense ratio might be completely different from yours.  

Originally posted by @Chris Seveney:@Patrick DesjardinsI was completely unaware of any issues when I posted what I posted.

I would recommend after completing their course that you check out www.retrainersca.com/ . 

Even though the houses are both completely remodeled, I would still set aside the extra $100/month for maint/repair. 

My insights aren’t complete guesses but are there any real estate pros out there with Massachusetts knowledge that could give me more substantial insight?

It depends on what your primary motivation is.The bottom line is that whether or not you can sell your home to a legitimate and ethical wholesaler is completely dependent upon the asking price and the ARV of the property. 

Is every house for rent on Craigslist just a complete scam?