You seem to be a perfect candidate for "DSCR Loans" - which are the typical option here for real estate investors looking to use an LLC vs. individual or some of the requirements you mentioned. 

I said perfect!

Congrats = probably not perfect but getting a profit out of the first investment property experience is generally a huge win

This is a perfect example, what do I/you do? 

This is a perfect response.

You are the perfect guy to answer my questions. 

There's no perfect answer to this question.

At the time, it was not so much thought of as an investment as it was a place I thought would be perfect to raise my children.

#1 - You are not required to have your driveway in perfect condition, it's totally up to you as to how nice (or bad) you want your property to look.#2 - As @Theresa Harris said, just pressure wash it if you do anything, if you apint it, you'll be painting it again in a year or two.#3 - Never let a tenant do anything to your property.

VA would be perfect for house hacking, or just building equity.