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. 

You can use changing smoke detector batteries or changing furnace filters as the reason to enter the property.

I was trying out a battery powered one (smaller lot) and left it.

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.

I don't like battery operated cameras.

Worth the extra money in my opinion and just need 4 batteries every year or two. 

I don’t recommend the handheld battery powered sprayers for many things other than very small projects.  

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.