I would like to use my VA loan this time around since I have to move to the area for work anyways (so safety for family is a concern) but there just seem to be a lack of a multi-family available all together much less a deal that would fit the VA criteria.

We have been in business for 7 years, have proven systems, policies and procedures in place, we have managed as many as 340 doors and would like to discuss the current opportunity with an interested and motivated Broker.  

I got my friend's building complete on time and on budget about a year ago, and then completed a couple tenant improvements for him.I thought I would have an advantage starting my own business up here because I felt the customer service, quality of work, and attention to safety of the contractor's here was below what I was used to.  

Since the first policy was paid by the seller, you didn't need to pay for it.

I also understand that an umbrella insurance policy is my first line of defense.

Usually they have several code violations which are significant safety issues- the biggest usually being a lack of fire protection between units. 

I've recently rented out the property but have not updated my Homeowner's Insurance policy yet.

Karen, you need a vacant house policy- not widely offered.  

I am beginning to explore the land trust with LLC as beneficiary possibility, otherwise a commercial/portfolio loan will be necessary with less favorable terms and rates compared to conventional residential financing.If I could do it over again and planned to only have one or two properties I would simply invest in a good umbrella insurance policy and call it a day.

A banks internal policy might be lower, but if you use a broker they are going to be using multiple banks, therefore you shouldnt run into an issue til you hit 10.Also consider if you are married, and you each qualify for the mortgages independently, you could conceivably get up to 20 between the 2 of you.