If I pay it off, I could maximize cash flow earlier, reducing financial stress and allowing me to focus on other ventures or simply enjoy life more.On the other hand, I know some people advocate for keeping cheap debt and using the extra cash to invest elsewhere for potentially higher returns.Why I’m leaning toward paying it off:Security: No debt = peace of mind.Financial freedom earlier: A fully paid-off rental would give me a significant monthly cash flow?

However, you'll likely be able to put more money in your pocket if your reducing your living expenses in a HCOL area.

Focus on tax-saving strategies such as cost segregation studies and bonus depreciation to accelerate deductions.By qualifying as a Real Estate Professional (spending 750+ hours annually and materially participating), you can offset your wife’s S-Corp income with real estate losses, reducing your tax liability.

This level of scrutiny drastically reduces the risk of renting to unreliable tenants.Realtors vs.

Manufacturing has gone overseas reducing wages. 4.  

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.

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

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.

Consider starting with house hacking to reduce housing costs while learning property management, or explore mid-term and short-term rentals for steady or higher income.

Use your HELOC to purchase the duplex outright for $118K.Your brother’s $50K down payment can immediately go toward reducing your HELOC balance, leaving a remaining balance of $68K.Create a formal lease-to-own agreement with your brother.