I guess I can keep my cash flow. 

If there is a renter in place, you may be able to do a cash out loan without changing who owns it. 

Yep, then you will probably need to move the cash.  

With actual cash, you just transfer it. yes, but you can still bid with lender approval - without appraisal contingency - you send in deal (app), it gets approved by lender its functionally the same as cash (except in true lightning speed situations where there is a quick auction with little time to prep but thats generally pretty rare I'd think)Right, but that's not cash or functionally the same as cash because the lender can change the terms at the last minute, as often happens with less experienced hard money lenders.

Any advice on how to navigate this while keeping the deal intact or potential transfer of partners would be greatly appreciated!

If so, there are no transfer taxes due. 

Buy your next property with all cash, fix it up with cash, and then do a cash-out refinance afterward.

Hello BP Community,I have a cash deal opportunity and I've never done a cash deal before. 

Congrats on your cash-flowing property in Chicago! 

Eventually, I’d like to start using the cash flow to pay myself and work toward replacing my day job income.