I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

Let's assume your expenses (mortgage, taxes, insurance, maintenance, vacancy, etc.) comes to a clean $600 and the property rents for $1,000.

Who covers the tax bill when they don't pay the tax bill or the insurance? 

I would also share pros and cons of paying taxes on the windfall versus owner carry.

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There might be some confusion around the 60-day rollover rule which allows you to move money from one IRA/401k to another (both pre-tax and Roth).

Then if you still 100K off, I would start dropping the price in a big way to get to an even playing field. 

There is a lot to say here that would take awhile to write but a few things:  1. 

Minimum of 3 night stays, limited number of STRs in a particular neighborhood etc.You need to get the license and pay the STR tax.

At a 7% annual return, this could grow to $908K after 10 years, providing immediate liquidity and diversification.Alternatively, holding the property could yield $825K net equity after taxes in 10 years, assuming a $900K sale, with the potential to defer taxes via a 1031 exchange if reinvested into another property.