I've been on this site since August 2015 but had the feeling I was too young at the time, as well as not being close to feeling I had the knowledge or money to be active on the forums or to start investing.

Hi @Chris Mason narrowing down an strategy is exactly what I'm trying to do that's why I need to gain more knowledge about this subject, I'm a very analytical person and just like playing chess I like to analyze all the scenarios, always thinking 1,2,3,4,5 steps ahead then set up all my pieces  in place and then go for the checkmate (In this case landing a good deal, lowering my risks and maximizing the profit or cash on cash ROI). 

Ideally there's a balance between the notion of Right First Time and Minimum Viable Product that should be struck whereby one acquires enough knowledge to act and then uses action to adapt and evolve.

You need to find someone with knowledge of the local laws where your rent property is located.If they have good credit, they are probably going to be good payers. 

Your knowledge of the specific market will be more illuminating to the why than those outside your market.

I too learned the vast majority of my real estate knowledge though bigger pockets podcasts, forums, and books.

Have to start building relationships somewhere.Additionally, I seem to be lacking in knowledge on when I 'need' a contractor/engineer/architect.I.E.

If anyone has a similar experience or knowledge about this, I would greatly appreciate it. 

Having lived on Oahu for the past year, we are excited for this venture.Knowing that there are many complexities in the law, we were wondering if anyone had any experience/knowledge on how to do this legally.

It's like when Brandon Turner says on podcasts that he knows to buy on this side of the street but not that side of the street.....that knowledge comes from physically being in your playground.The thought of just picking a spot on the map and saying, "Yep, I'm going to invest here because the numbers say I should" without ever living there myself scares me.