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The single biggest advantage of selling your homestead is that you can take all the Cap gain tax free if you have lived in the home as your homestead for 2 of the last 5 years. 

If you're lucky enough to get a free and clear property where the seller is willing to finance, this reduces much of the risk associated with seller-finance.I would make sure the title is then moved over to your name, especially since there is not a risk of a due-on-sale clause being triggered.

Be sure to explore all around the forums as well as many of the FREE tools that Bigger Pockets provides.I am on the lending side of things and am always happy to hop on a call to discuss loan options that are out there, even if not offered by my resources.

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We have renters there now and they cover the mortgage with a bit of cash flow ($100/month), but the property is going to need some more major updates (windows, roof, HVAC, siding) within the next 5 years as they are starting to be at the end of their useful lives.We would like to pay off our primary residence as quickly as possible to “free us” from mortgage payments on our primary residence.My questions are below:1.

I'm in the greater Boston area and I wasn't able to fully live for free but I was spending about $700 on my unit.

I have a buddy who does this for a living on raw land, and he pays for the software and gives us all the data for free.  

Fast forward a few years we are we financially free via house hacking and owning small businesses (leveraging our house hacks as collateral). 

That home was in Milpitas CA.. probably worth about 1 mil today.. but I lived there 2 years sold it made over 50k and I was off to the races.. primary home equity as I look back 50 years of ownership and multiple homes has made me well over 2.5 million in tax free gains.