Opened up the tiny kitchen to the dining room...

@Akeem Watson you can make money anywhere in Chicago as long as you know the areas and are comfortable with them.

This includes individuals who primarily have W-2 income from employment, basic investment income, and perhaps own a home or have standard deductions.Rental Property: If you have one or two rental properties and feel comfortable managing the related expenses and deductions, tax software can handle this level of complexity, especially if your transactions are straightforward and well-documented.Complex Scenarios: Hiring a CPAWhen to Consider: As your financial life becomes more complex—such as owning multiple rental properties, running a business, dealing with investment incomes, or having special tax considerations (like inheritance or foreign income)—the benefits of hiring a CPA increase.Cost Consideration: Hiring a CPA typically costs at least $1,000 to file your taxes, which can increase based on the complexity of your return.

@J Newman to answer your HELOC question: yes, you can use those funds for business purposes if Dad is comfortable with that option.

Sometimes people who are comfortable managing the details of a job will hire a less skilled person to do it knowing they can get a MUCH better price and a "decent" job IF they themselves stay on top of how the work is being done.

If you're looking at investing in MA or any state, I'd probably wait till you have enough for 25% downpayment + closing costs and about 70-100% of capex reserves + vacancies set aside comfortably.

This allowed me to feel comfortable buying the house and not having to worry about rushing tenants into the property.

Once you are comfortable with running real estate, you can consider having one of you leave work and manage the properties full time.

Unfortunately still very very challenging on the SRO Front - I am still working on getting the capital markets side of the equation comfortable with it, but work in progress

Maybe determine a cash-on-cash figure that aligns with your comfort level.