If the goal is living for free, then I think buying a single family and renting by the room is the only option to achieve that goal. 

IF that future is better achieved through real estate investing, then that's fantastic!  

I find that creating and sustaining a respectful, honourable and extremely professional relationship between the two sides in a transaction is probably the biggest determining factor in getting my clients the very best deal that could be achieved in the circumstances.I am truly sorry you're in this spot, hope this clarifies things a little for you.

@Richard TibbettsIf you want to defer all of the capital gains tax, you have to receive $0 boot.You would need to spend 100% of the money the intermediary received from the sale.You would need to purchase more than $330,000 if you want to achieve this.

My goal is long term buy and holds but I am using wholesaling as a tool to achieve that goal.

We have a strong diverse employment base, growing population and properties are still priced at a point where good cashflow and appreciation can be achieved.

Is there an investor in your area that is a close model to what your trying to achieve?

It's a good initial indicator of a good deal but you'd need to be able to determine the amount of rehab required to achieve the higher price point in order to determine whether it is a good deal.

WHEN in time will it likely be achieved?

Sit tight and let the levers of house hacking + real estate investing work for you.To optimize your house-hack experience to better achieve your goals, I'd recommend pretending like you have a standard mortgage payment for your area and stuffing the savings your realizing every month into your investing account, sock drawer, or other preferred method of stashing cash.