Options like a unique amortization schedule or a 3/2/1 or 2/1 stepdown interest rate could provide initial relief to get you through the renovation phase while giving the seller confidence in a structured payoff plan.To determine an entry point, consider reducing the price based on the current NOI.

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

If your manager is just 'keeping an eye' on things, collecting/reminding on a few rents here and there and some light cleanup while being compensated in free or reduced space rent then classifying them as 1099 subcontractor is great. 

Quote from @Aaron Zimmerman: I would look for other ways to legally reduce income such as cost segregation studies.

It’s gotten me seriously considering bringing an attorney in-house to handle evictions and other legal needs moving forward.I’m evaluating this from two angles:Cost Efficiency: With the expense as high as it is, having in-house counsel could potentially reduce costs over time.

Using a 1031 to upgrade to a two-family could help you reduce or eliminate the $1,000 out-of-pocket expense you’re paying now.Also, condos often come with HOA fees that limit cash flow, so be mindful of their impact.

If we do cost segregation how much would we reduce our taxes by?

Also with plans to reduce industrial "intensity" in and around residential areas. 

Is there a way to reduce the amount of hours so you have more time for other activities?

The implication is to lower rents requires reducing the cost of ownership.