Then, I would evaluate my financial position and see what the best way of getting started would be (in terms of property cost, risk, etc...).

However, my area (high cost-of-living) could make breaking even or positive cash flow difficult.The main question: is house hacking worth it or a "good deal" if cash flow from the rented units doesn't fully cover all expenses but you're significantly reducing living costs?

Value add investments typically have in-place cash flow and that cash flow can be increased over time by re-positioning the property and through operational improvements. 

Then exactly like @Ashish Acharya said you do a cash out refinance (making sure that the cash out still leaves you positive NOI)  and take the extra equity and buy your next rental. 

For riding out a crash, position yourself properly with solid cash flow, 8-12 month of P&I reserves, desirable properties, low leverage properties and solid financing.

Any strategies or insights negative or positive is welcomed and helpful.

We landed on selling as a solid option that shouldn't have a significant tax impact with the new tax law (and the fact that this will be my first flip).

From what your numbers are showing, it looks like it could be a pretty decent deal for your long term buy and hold position.

@Steve Rozenberg,What has impacted us is when someone makes us "an offer we can't refuse" on a property we own

The landlord is not communicating well and is not consistent in his position.