Capex, existing contracts and lessors, value add proposition.  

Dead, gone, and never should have been in existence in the first place.

In Metairie, duplexes exist, but true multifamily is less common; the area is more single-family focused.

Check Edgewater's zoning code to confirm accessory dwelling units (ADUs) or duplexes are allowed in your specific zone, as some single-family residential zones prohibit separate rentals even if the structure exists.

why would you build in Chicago when existing buildinds can be bought for a fraction of what they would cost to replace or replicate ? 

Your area may be different, where building small MF can be done for less than the cost of buying and upgrading existing. 

Also, after closing, would I need to place all tenants on new leases since their existing ones were with the previous owner and may not be enforceable?

Is the co-hosting approach the best/cleanest way to handle existing reservations?

As mentioned, shockingly, there is no option to transfer a listing (as simple as it would be for Airbnb & Vrbo to create).What we do is get the guest contact information and booking details from the previous owner/host/property manager, and draft a message to existing guests from the previous owner/host/property manager, explaining the situation and asking the previous owner/host/property manager to send it to the guest then almost immediatly after we reach out to the guest following up ideally by phone. 

Would you Refi the existing property to use that cash to buy more or find a DSCR loan.