My property will have 5 units total once we finish converting our garage to an ADU -- we just finished building a 2-unit ADU structure that's all new construction, and the property already had an existing duplex.

Rent: $1400, HOA: $300, Insurance/Tax: $144, Net Monthly: $956, Net Yearly: $11,472, ROI: $11,472 / $106,000 = 10.8%Potential Condo #2: $115,000 purchase price, Rent: 1400, HOA: $260, Insurance/Tax: $150DSCR Cash Out Refi on Condo #1: LTV 75%, $86,000 Loan Amount, 30 yr fixed, 7.5% rate, Monthly Payment: Around $650, Closing Costs: Around 8-10k, Total Cash Left: $76,000Condo #1 After Refi: Money Left In: $28,750, Monthly Net w/ Payment: $306, ROI: $3600 / $28,750 = 12.5%Cash In Hand: $76,000DSCR Loan on Condo #2: $115,000 purchase price, 25% down: $28,750, after fees estimating $35,000 All In, $1400 Rent, $260 HOA, $150 Insurance/Tax, $650 Monthly Payment, Net Monthly: $330, Net Yearly $3960, ROI: $3960 / $35,000 = 11.3%RESULT: Total Monthly Costs: $2160, Total Monthly Net: $630 ish, Yearly Net: $7,560, Total Cash Invested $65,000, Yearly ROI: 11.6% CASH LEFT OVER: $41,000Could put the cash into a third condo or put into the S&P 500.Looking for some guidance on whether or not I should pull the trigger for some context:19 years old college student studying engineering (heavy courseload)Living in Chicago, Condos are in Ohio (I have family and friends out there)I work part time at a high end hibachi restaurant averaging $25-$30 an hour.My rent + utilities with roommates is $750 with room mates.The numbers work out, my main concern is whether or not Ill deal with large vacancy within the next 5 years, or a recession, and I have to cover the monthly costs on my own ($2,160) which is a lot and not sure if I would be able to keep that up for a long time if I am not working full time in the industry.

You're totally right to want clarity on all the layers of regulation because they will affect your bottom line.Rent stabilization is the biggest thing to watch.

I don't know if I totally agree @Jim K.

Quote from @Shlomo Rozen: I don't have cash on hand for a deal but I do have at least $100k of equity available in my primary residence that I could extract as a HELOC.

Totally worth it.Hope this helps!  

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I do appreciate that you and your family were handy enough to lend a hand though.

On the other hand, house hacking a 2–4 unit property in your local market lets you live in one unit, generate rental income from the others, and learn the ins and outs of being a landlord hands-on.

Typical downpayment is based on the project cost which could go up to 1/3 of total cost.