However, I'm not really in a position to do a live in flip here because my wife and kids love the house :)

Can you figure out for example who has seniors in high school and do they have any other kids at home. 

The upper level of society works in ways most of us will never understand...it sadly continues to be a back-and-forth thing of reaction...If our country and Chicago as well could take a proactive long term approach, our kid's kids would benefit in a way we couldn't image....

Kid in college and one starting to drive   blah blah blah.I'm sure there are numerous places to cut money for sure. 

Second is that you can be disciplined enough to take the money that is left over and not spend it on "stuff" so that you can have it to put down on your next property that you are going to house hack and that you will do it when you get to your next destination this summer or fall.

My parents have an apartment in Vancouver that they are debating whether to sell it or pass it onto their kids.

With a family and kids the best house hack is a house and cottage or duplex option.

Usually it is a leftover from a child or grandchild getting a mobile home and then graduating to building their own home. 

It was so bad, the kids would even tell me to stop buying rentals because they would hear her complain to me every time I bought a new house.

People have mortgages, kids in college, caring for elderly parents or kids with special needs/ Many of them now have no idea what life is brining for them in the near future.