We were looking at it more for the flexibility of looking at a lot of properties frequently, MLS access and being able to continuously put in offers without exhausting an agent who has other clients to focus on as well.  

Definitely exhaust all the areas near you first though even though I know your area is super expensive maybe you'll get lucky and find a good deal. 

Sorry this is months late however I'm jumping back on track now after months of learning ,working to pay my bills & exhausted burnt out Life Challenges! 

Things actually work the other way around from a typical contractor's mentality thinking they are financing the client when in reality they are expecting a client to finance the contractor's business. 

Get data on insurance claims, flooding, etc.My personal view is that leadership within a city/municipality needs to have more of a 'we all rise together' kind of mentality. 

The goal with paying it off would be to jump the mental hurdle of owning a property free and clear, start an LLC and transfer the title into that LLC, and then to have a property that we can HELOC against in order to have the flexibility to make cash offers so that we can begin making LLC purchases more easily rather than titling in our own names.I'm certain that plenty here would advise to continue rolling the money into new properties, rather than to pay one down, since owning the house free and clear would provide about half the cash flow that we could get from down payments on two new properties, however my wife (in particular) and I both like the idea of simply owning one property outright and then using the above strategy moving forward. 

He is a good guy with a residential tenant mentality whose business is struggling.

I get it, the forum is here for the discussion but I want to encourage you to make every effort possible to find the answers on your own, exhaust all efforts to get the information you are looking for before asking people to answer the question for you, more often than not you will find the information on your own or you will refine your question to the point that it becomes interesting enough for people of solid intellect to respond to.

As far as capital to get started, after you've exhausted the VA loan, the typical and common answer for a primary residence is a 20% down payment with a credit score and cash reserves good enough to qualify for a mortgage.

Here 's a mentality shift that's necessary for you.