I’ve had a slight shift in my investment life and will be making less extra payments as I move forward and continue trying to scale.

You can switch to a lawn service and the major issue will be they have to move their stuff when the lawn guy comes.  

Chicago real estate is moving quickly and it's honestly no surprise rents are too...with less inventory for sale that also means more people are forced to rent, which in my opinion would drive up the rent.  

I'm not a realtor, so we are not allowed to use the GAR forms, and their forms often contain a non assignment stipulation.

@Marv Edelstein Congrats on making the move to multifamily!

That's only 45 bps for 30 days, rarely is it this cheap. 2) If you have time to move somewhere else, you can A) go to another broker and get other non-QM quotes and threaten to leave the current broker if they do not give you a free extension/come down in pricing as rates have improved, or B) Tell current broker to get other quotes from other non-QM lenders they work with.

I currently own a home in Hawaii, unfortunately my family and I are moving and we want to make the correct choice.

You are making the right move by going to RE, IMO.I think you have the right idea on the strategy. 

When a tenant moves out, transfer the deposit back to Checking so it's ready to apply towards expenses or refund the Tenant.If you end up with excess funds in the Checking account, I recommend you transfer it to a third account designated explicitly for future investments.