Dive in and write a story about the property and see if it fits into your life. 

Goal is always cash flowing quickly!

I have been coming across 8-12%  and that doesn't fit my buy and hold strategy.

I see a lot of post mentioning being new to the industry and having a goal of 20 houses within year 1 of their portfolio and their starting out with no money at all.

My short term goal is to try to master wholesaling and then move into cash flow properties.

That is speculating and not investing.Numbers work going in and the rest is icing on the cake if it happens and if not you hit your goals anyway.It seems the primary reason you are buying is for a home for the family to live in so the investment portion seems like a much less important detail than the emotional component from what you have said so far.Maybe just view this property as a happy family home purchase and then if you like the area once you live there look around for properties where you buy just off of investment from the additional cash flow with the low mortgage payment.

Aloha - I'm considering a few projects in Maui and would appreciate the recommendations of any general contractors who can fit the ROI-based business model of investors (i.e. not going for magazine covers).

I'd be happy to have a conversation with you to see whether we'd be a good fit and if so, will be prepared to get to work immediately.

My goal is to ultimately invest in multi-family units and eventually apartment buildings.

I am using real estate as a vehicle to reach my goal of financial freedom.