Speaking as a new investor, I am relying on my Business Administration/Finance degree to help me understand things like time value of money and analytical considerations.

Studied it in school, was an MLO for a period of time and have been at a large CRE research and analytics company the last few years. 

It is important to understand your target audience - if they are analytical, then text and numbers would be best.

The techs believe you can create a "program" to substitute for the knowledge, experience, analytical ability and deal making savvy of successful private lending professionals, so far this has not proven correct.2.

The market here has traditionally been very steady, and the specific location (two blocks from major university, downtown shops/restaurants/bars) within the market is superb.

If you look at this analytically enough, there is not difference, and your preference is to rent temporarily, then go for it.  

I've seen a few Honolulu properties of interest and did the BP analytics.  

For example, I am very fluent in the analytics of evaluating an investment opportunity, the financing options, etc,.... but I have no idea how to form an LLC (attorneys typically do it) or how to draft a lease or how to collect rent (we use 3rd party property management that handles).  

I have also teamed up with an investor and we have closed on 2 deals and have 3 under contract at the moment.I don't really have funding for these deals, just a good sense of analytics.

There are services that provide analytics on occupancy and types of rentals.