I'm 32 and Need to Know When to Quit My Job and "Retire"

[Mike Honcho]

Before I give some context and background information on my situation I want to preface this with what retirement means to me. To me it is the freedom to what I want want and how. To wake up and my days are filled with working solely on my projects and goals. It doesn't mean I will stop working, I'll just stop working for somebody else.

I'm 32 years old and married with 1 child on the way and I live in Canada. My wife is employed full time and makes about $75k a year with pension and benefits. I work full time at a decent desk job making about $100k a year plus a small pension and benefits plan. 

I've been investing in real estate for about 7 years now and I have over 10 properties. Mostly a mix of single family and small multifamily (duplex type homes). They don't all cashflow as much as I would like as I have refinanced to purchase more or for other renovations. 

I have a side hustle that is real estate related that with more free time I could grow and build on to generate income, probably around $100k annually.

I know this question is often highly debated but my dilemma is do I sell off one of my properties to pay off my home mortgage. I get the whole use cash flow to pay off your monthly expenses and the equity in my home could be reinvested somewhere else etc. I feel selling off a property and paying it off (or at least a large portion of it) would give us some freedom, and a feeling of accomplishment. Our living expenses are low and we live within our means with no other debt obligations other that investment property mortgages and a personal mortgage.

I also have trouble selling a property knowing that it will very likely continue to appreciate, increase in rent and cash flow and lose on the continued principal recap.

Anybody else in a similar situation. Any advice or input would be appreciated. I don't have any friends or family that truly get this sort of thing so that is why I've come here.