@Rachel Jane a lot of issues here to consider:1) Does the condo association even allow rentals?

There is almost no scenario where a condo would ever positive cash flow while servicing debt, and very little positive cash flow with no debt.If your budget only allows for a condo, find a better place to put your money to work.   

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The challenge was balancing the relationship between landlord/tenant and a personal/friendly relationship.

The modest cash flow could be reinvested, eventually allowing me to build a portfolio of income-generating properties.I recognize your point about needing $2.5M–$3M in cash to consistently replace a six-figure income.

Our only debts are a 2.875% mortgage with a balance of $124k only paying $897/month on an appraised value of $325k, daily driver car of $370/month, and use a credit card for monthly expenses, but pay the balance off with every pay check.

It should detail any liens or subordinate agreements, including the unpaid balance.

Ultimately, it's all about the right balance—staging should always be tailored to the home and the market it’s in, which is where working with a knowledgeable agent really makes a difference.Would love to hear your thoughts as well!

.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

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.