I know, there are plenty of red flags there, but I do believe it is worth the risk when I consider how happy it makes my wife, how life-changing it will be for the family, how minor the financial impact will be on me, and how it gives me the opportunity to practice the steps of real estate investing with forgiving tenants.Finally, I am going to attempt to self manage as nothing comes close to cash-flowing if you include PM costs.

Stories like these are what make house hacking worth it.I hope this helps, Tim!

The price/how much you will get out of it is probably not going to be worth it.

If you pay that before the end of the month, the reported balance is going to be $0 even if you buy $5k worth of Christmas presents next week, because that float won't count until the next statement closes.

The 3rd thing that has reshaped my entire opinion of the tax advantages of real estate, is seeing my 88 grandfather holding five quite valuable illiquid properties, long story short it’s a mess, it’s causing family drama, he is in zero shape physically or mentally to manage them, the all have cap-ex needs, again these were amazing buy’s literally multiple properties he bought for under 50k that are now worth over a million but there is probably a time and a place for owning real estate, so I don’t really have a need to own more than maybe a few properties into retirement.

I equated it to a property per year simply because in the Denver area it's very difficult to find cash-flowing deals that make the investment worth it, so I figured I'd be looking at several properties to reach my financial goal. 

If you think you might get kicked out then housing security might be worth upping the payment. 

I currently own a duplex in Philadelphia that is worth $285k conservatively.

Quote from @Levi Perl: Hi,Curious if anyone has what to say in terms of how to calculate which one is more worth it: to cash out refi on a Long term rental now at 70% LTV, and walk away with X amount of positive cash AFTER paying all debt, (X is a positive number and significant amount for me), which will allow me to potential get another long term rental and grow portfolio faster, or wait 4 months and cash out 80% LTV, giving me DOUBLE than X. 

We still had the meeting and filled all the paperwork out though so it's worth a shot