Rent is decently expensive, but whenever I booked the stay, the owner mentioned he was trying to sell the unit.

I have read and am currently reading books on real estate and real estate investing.Following my readings up to date, I am considering house hacking for my first deal in real estate.

., I'm so glad to hear that our booked helped you take action!

I've read J Scott's Books on flipping and gone through the Youtube rabbit hole but I feel like I'm missing a piece.

Since traditional agent training doesn’t cover investing, supplement your learning with books, podcasts, and investor meetups.Good luck!

If I sold, I think it would be by a hair that I can offload the property for the balance despite a tax value of $440,000, but it would get it off my books completely and free up my VA loan to purchase again. 

@Raul Velazquez The 3 things I would recommend besides reading books/audio/sites are:1.

Not sure I would use up my full emergency fund for a down payment, owning 2 properties and not having any funds for emergency is not advisable in my book. 

You need to learn how to analyze property and determine if they are a good investment.Here's a guide that describes how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...

Wasn't there a book something about 10,000hrs of practice or maybe it was a chapter in a book.