I've done some flips in Hawaii at much larger price points but the Midwest in my opinion is still one of the best markets for cash flow. 

Flips have done good not great, Air Bnbs are going good not great, and rentals all were brrrr'd perfectly but like most cash flow just enough to pay the bills and cover expenses.

I own 4 two/three flats bought between 2013 and 2020 in Forest Park, Illinois, at low interest rates and prices in 200000's  They cash flow nicely and prices have increased a lot. 

Still good cash flow. 

The allure of fat cash flow (at least on paper) and the low barrier of entry (down payment) never stop attracting new investors. 

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

So seems like a decent play for cash flow but not much for appreciation.

This creates an initial negative equity position that consumes the initial cash flow, sometimes for many years.

I think real estate investing is absolutely the way to go thanks to the cash flow, appreciation, and tax benefits! 

I would restate that the lease will remain in place until such time that a new tenant is selected and moves into the property.This approach will ensure your cash flow while acknowledging that 'stuff happens.'