As for numbers, I currently owe $86,151 on the mortgage, and on Zillow it is listed at $143,600 but the numbers seem to be inflated on that site.  

I think another trick is, can you get a mortgage or is it an all cash deal?

The mortgage servicers, agents, buyers, sellers, etc.

A common strategy I see with diversification exchanges, is that the investor will purchase the first property cash and the second with a mortgage.

I know I could have a family member co-sign a mortgage with me but not sure the best way to approach that conversation and what incentives I’d be able to offer to make it worth while for them other then their “familial duties” haha. 

I found a decent duplex in Pennsylvania. it was newly flipped and was a pretty decent price in an okay area. the mortgage is around $2,400 and I was able to rent both units for $1500.

I’m also open to exploring short-term rentals, private lending, or passive investing in funds—anything that maximizes returns while keeping risk and time commitments manageable.For context, I’d consider leaving my job if this could become a full-time venture that surpasses my current compensation (low-mid six figures).

Over time I have amassed a good quantity of houses with no mortgages.

I had specifically asked for numbers including mortgage payments and they emailed to me.

Read your mortgage paperwork for the due on sale clause.