This is counter-intuitive to my goal - slow and steady save to purchase our first investment property (with more to follow). 

A property or two will not be your ticket out.

I have a property in Fort Wayne that I own free and clear.  

It needs a lot of work, but my main thing I need help with is this old shed behind the property.

It will just be more of an explicit part of the price negotiation when buying a property.

Purchase price: $38,000 Bought this property with a private monery lender and sell it to a investor with 20K down.

I didn't phase that correctly and should have put an emphasis on "Traditional Sale".I am willing to sell but want to do it "creatively" - if you will - to generate funds and positive cash flow from the note I would hold against the property.

I have different strategies in mind but my main concern is if I should start an LLC now or after I buy a few properties?

Own property and needs full renovations2.

I'm looking to use my VA Loan for the first time to purchase my first property.