@Fady MikhailConsidering utilizing a 1031 exchange and using all of the tax to your advantage by reinvesting it into something with some cash flow potential is wise.

Quote from @Remington Lyman: Quote from @James Wise: Quote from @Remington Lyman: Quote from @James Wise: Quote from @Remington Lyman: Quote from @James Wise: Quote from @Remington Lyman: Quote from @James Wise: Quote from @Remington Lyman: Quote from @James Wise: Quote from @Remington Lyman: Quote from @James Wise: Why do we allow people who can't even afford to take care of themselves and their families the opportunity to vote? 

Assuming we’re heading into some headwinds, is this a wise direction right now?

Quote from @Remington Lyman: Quote from @James Wise: Jesus Christ the Columbus Cartel pouncing like a pack of Heyenas. 

Is this a wise decision to use a HELOC on property number one that only has 20 to 25% equity in it to fund a down payment for a live in house hack in multifamily property number two?

Number-wise, @Ebonie Beaco gave you a good ballpark. 

It is clear to me that counting on rental /cash flow is not wise at all, .  

My wife and I both want to hold quality assets for long periods of time, so we are considering that as well; we don't want to purchase a property that simply looks good numbers-wise, but isn't in a desirable area of town (both for our sake and our future tenants' sake too).

Most are nightmares b/c the investor taking the project on isn't ready capital wise, mentally, or infrastructure wise. 

If so, my opinion is that you are being penny wise - but pound foolish.A more basic questions is WHY - why are you forming this “partnership”.