I am also looking to rent out a single family home or a small multi-family at some point but I would like to have some money to put down.

Then to make matters worse, she went on a work trip and when she returned the water heater busted and had a small leak that ended up flooding the pantry and kitchen which ruined the flooring.

If you Google VA county loan limits you should be able to find a website that will tell you what the different limits are for a small multi family in your county. 

Then I want to talk about the little quarks that you can use (such as including potential rental income to qualify, buying small multi families, second tier guarantees) to build your wealth and invest.

Perhaps it’s big enough to build a small self storage building on ?

I don't mind that because I have a "start where you can and do what you can do" mentality (and as I have heard so many times even on these boards, "all it takes is one deal to turn everything around no matter how small your marketing").

This buys a small 2 bedroom here in our area.  

I'd like to start by creatively obtaining a property with a small initial investment, so any advice would be appreciated!!

So region ,  time in the cycle  and desire to work in your own job.Most of my closer friends or colleagues are self employed small business owners.. 

Of course, you could argue that with multifamily you're also spreading your risk and might have more upside, but there's definitely something psychological about starting on the small end and working yourself up.