I'm in the union on long island so I have a decent W2 job to help get started, I think a house hack would be my best bet starting out but, what do you guys think?

All the best,Chris

The best way is to converse with like-minded people to share visions and thoughts.  

We added value by making a accent while in the living room, as well as refreshing all the furniture and decorations, painting the property, making a back door. back door out of the master bedroom because there was no way to get to the backyard without having to go through the side as well as some landscaping & new washer dryer.

At this point, a house hack might not be the best option for me because the housing costs in California are too high.

Plus if they book through somewhere like Airbnb or VRBO they we have the insurance to protect stuff that way.

What are the best websites that monitor trends in populations and real estate for USA?

This might help narrow down the best fit in terms of lender type.Do you have any prior construction experience or a builder on board?

I also noticed the grass had grown over the sidewalks so you could not see them, and in some areas was creeping got on to the roads the same way . 

Learning from someone who is already doing it in your city would be the best next step.