I didn't feel comfortable lying about the purpose of the home since I have no intention of staying there and purely plan to use it for investment. 

We planned a purely cosmetic re-hab, and whoops.

@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.