2 for 1 Off Market deals in 2 different markets

[Rob Greynolds]

Hello, I have an opportunity to purchase a nice single family home in a desirable area in the Chicago suburbs off market. The person wants to retire in North Carolina and is willing to sell her house to me by owner. After some further discussions we discussed her goals and realized we could also partner on a house hack deal in North Carolina. My question is what's the best way to the purchase the Chicago property? She would be willing to quit claim deed her house to me as we have a very trusting relationship and I want to make sure I give her a fair and honest deal. I was thinking a cash offer for the Chicago place and then a cash out refi(if the numbers work) for North Carolina.
 

Looking to talk to someone for guidance!