It's obviously not ideal.  1.1 dscr and likely around 7% with a 25-30% down payment. 

You might be better suited to just buy a Turn-Key home and do it yourself. 

I know a lot of this decision is based on personal variables, but I'm wondering whether there are any tell-tale signs that a specific property is better suited for one particular investment strategy. 

Ideally you have the reserves. 

It friends with social networks (Facebook, Twitter) and Office 365 and G Suite Teams.Act CRM.

It seems after listening to a few of the podcasts there are alternative solutions that would be better suited to start and grow and wouldn't have to wait the 2 years to refi.My logic was that the VA Loan is $0/down on your 1st mortgage and 20% down on a second mortgage and I didn't think I would be able to afford the 20% down on a property in Hawaii.

Their job lost may have come at the ideal time for you and them.

Or if you're set on going upstairs then just add the master suite upstairs (500-600sq ft) and finish the downstairs.

So I am looking to buy my first property (ideally sooner than later) ...

And ideally, have before pictures available.