Very unique living/renting situation – when do I buy a home?

Very unique living/renting situation - when do I buy a home? My wife and I (mid-thirties) live in a VHCOL area, but fortunately I have a side-gig where I manage the building we live in for a third-party owner, so we pay nothing for rent or utilities (water, elec, gas, trash are all covered and up to $100/mo for internet stipend). My wife and I make roughly $100k/year before taxes, so we do decently to sa...

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