I think having a balanced budget would be ideal where you allocate money into buying another property and money set aside for renovations.

Actually, it is possible do structure a 1031 Exchange on the sale of one or more relinquished properties and then using the proceeds through the 1031 Exchange to construct improvements on real property you already own.

Offering discounts for weekday or longer stays could also help improve occupancy.

The property itself should bring in revenue ( even if you choose not to live in one side) and generally a bank will accept a portion of that rental income into the calculation. 

Depends on which property you pull equity from.

As a investment property lender we saw a lot of success with flips but an even bigger jump in BRRRR success with borrowers holding as long term and short term rentals. 

The 1031 must be a sale of investment property followed by the purchase of investment property.  Improvements

Are you looking to pay off the hard money loan, fund another investment, or cover property improvements?

Congrats on your cash-flowing property in Chicago! 

The improvements needed to be completed within the 180 day timeline, so I did a pre-fab ADU.