If you paid down a large chunk of your student loans, continued to save a little and increased your income you'd be in a much better financial situation and you wouldn't have to stress about financial issues and struggles.

I think i may be struggling with the mindset of having a mortgage and having a paid off house.  

I have read several things on this great tax benefit but I am struggling to understand the process of putting it into action or documenting it correctly.Can anyone help walk a rookie through this?

But yes trying to put concrete numbers into the equation is what I'm struggling with.

You are not alone in your struggle to find quality deals.

I would be investing profits in either multi-family or airbnb friendly single family houses in Los Angeles area where I'm struggling to find deals (although I know they're out there).

We struggled for years paying extra to the mortgage and could not sell it at all while the capital gains benefits were still there.

I feared a life of never ceasing hard work, struggling in the rat race to get ahead, and doing so for the majority of my life.

However, when calculating ROI and IRR, I've struggled with a way to account for the "rent" I'm saving.  

We are struggling a little with what our purchase price would be, on one hand we don't want to take advantage of the family connection to where the deal wouldn't be a win, win for everyone, but at the same time we'd obviously love to buy homes that have an incredible amount of equity going in.