Here’s my two cents:Paying off the condo might make sense if your main goal is to reduce risk and enjoy the peace of mind that comes with no mortgage.

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. 

Hey Deirdre,To address your questions:Providing freedom by handling day-to-day operations.Offering peace of mind through proactive maintenance and tenant communication.Reducing risks by staying ahead of legal requirements, tenant screening, and dispute resolution.Enhancing the bottom line by identifying cost-saving opportunities while ensuring tenant satisfaction to reduce turnover.Is the experience still important when the property thrives financially?

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.

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.

Many PMs ask for this in their agreements to reduce their own liability exposure.

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.

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

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.

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