@Joshua Karas You're on the right track. 

We're starting late and looking to shorten the retirement on-ramp.  

Also, the insurance was a lot less on a brand new home compared to an older one. 

Seems like the new on line marketing methods  Section 8 is the new shinny object..

Congratulations on your flip.

@John Zhang If your wife qualifies for Real Estate Professional Status (REPS) and materially participates in managing rental properties, there is no limit on the amount of rental losses, including depreciation, that can offset your W-2 income.

If I refi cash out I can probably only get about $50k out of the investment property, any ideas on another way to get the amount I need that I may not be thinking of?

If we are losing money every year, but do plan on holding on to it long term, with our goal being appreciation of the market and someone else paying a good chunk of our mortgage, is this worth doing on any level? 

would love to connect. best of luck on your journey

Wise lenders have borrowers sign legal agreements and have them provide collateral that is worth more than the amount of the loan in case the borrower doesn't make the promised payments on the loan.