The others should be evaluated based on what you feel comfortable with having as tenants on a more basic level in terms of character and behavior.

If you are looking for a way to more efficiently run your own comps in a more "user friendly" way, have you looked into HomeSnap?

you do not want to go with the cheapest option all the time because cheaper paint is thinner and will need multiple coats compared to a more expensive paint you might need one or two coats. labor is much more expensive than materials When painting an accent wall in a rental property I try to pay attention to what walls are going to take most of the damage.

New furnace, windows, flooring, modified the floorplan for a more open kitchen and a master suite.

It will be a more centralized issue.

Going with a more expensive, but reputable contractor, versus saving on the cheap labor. 

Rentometer is good for a quick number but I like to do a more detailed analysis through listing sites. 

Does this sound like a more realistic/practical option of bringing them in on the house hack or would it be smarter to keep my own duplex investing goal for myself and invest with my two friends separately? 

Andrew, you need a more creative debt strategy.

Figured this method was a good way to clean up property while living in it, elevating value and instead of going flipping route build a more long term steady form of the income.