@Ben Rhodin I am looking for pure cash flow and care less about appreciation for sure.

I've been purely in the mindset of cash flow positive only properties, but seeing a principal payment of over $1,000 on the first month makes me wonder if this is a decent option. 

Just from a pure market standpoint, your are going to be hard pressed to find worthwhile duplex/single family homes in your price range from Greater Worcester -> East Mass.

He has 1 million of pure profit sitting in the bank, not doing anything. 

Purely for cash flow, rent for the SFH would be ~1.4k, and each unit could be rented at around 900, so I guess if the rehab + permits and all that process make sense number-wise I would go for it.

Unless you are creating some kind of world vision - think the Teslas, Googles, etc - the arrangement is almost purely transactional; they are looking for maximum dollars for minimal work, and you are likely looking for the opposite.

I am working purely from my own funds so I feel like house hacking will be the way to go.

Also, not all incentives are purely financial.

This could be an LLC jointly owned by the contributors or a Joint Venture agreement, but you'll be thankful for this structuring 5-15 years from now.If you are using OPM to take down a property and you'll be cashing them out, then you don't need a structure like this necessarily -- a promissory note and related instruments can be used and then once the cash-out happens they are paid off and released and you own it pure and simply.

@Ruben S Paul buying land in this area, like @Will Fraser mentioned would be purely speculative.