Fast forward to 2016, I'm two years away from paying it off (extra principle payments) and my oldest child graduates high school in 3 years.

Maybe should mention (or not), that I am undecided as to whether I want to continue living in the U.S. beyond 2017.  

After our only child got married, we of course started to talk about grandkids...my son had moved to Nashville, and we were still on the east coast - so the wife had the urge to move closer to our son - we pretty much sold it all, liquidated while the market was still strong and moved again.

Current opinion is such a dual Parent-Child transfer would not be considered a Step Transaction.  

http://obamacarefacts.com/obamacare-individual-man...The annual fee for not having insurance in 2015 is $325 per adult and $162.50 per child (up to $975 for a family), or it's 2% of your household income above the tax return filing threshold for your filing status – whichever is greater.http://www.cbsnews.com/news/is-mandatory-health-insurance-constitutional/

Yes they are moving but they have a child which will make it a little more difficult to move again.  

Total monthly debt includes expenses such as mortgage payments (made up of PITI), credit-card payments, child support and other loan payments.

This can be your spouse, your child, your parent or a trusted friend.  

He only had one child, the rest were siblings, etc.

I am looking for a potential new house for me closer to work and my childs private school.