I'm breaking this into phases where I am learning for a couple months, to include,  speaking with others with experience and then "going for it".

@Del Brady what your dealing with is old news!

I think the best approach for house hacking nowadays is buying the most expensive 3-4 unit building you can that still at least breaks even as a long term rental from day 1.

I’m Micah — a real estate investor, coach, and proud Chicagoan.I started my investment journey back in 2024, and since then, I’ve:- Built a 7-unit rental portfolio in Chicago (Logan Square & North Lawndale)- Founded the Brick by Brick Blueprint, where I coach first-time investors through buying their first rental- Helped close over $175M in institutional real estate deals through my work in acquisitions at a real estate private equity firmThese days, I spend most of my time helping new investors build confidence, analyze deals, and get to the closing table — especially folks in their 20s and 30s who are juggling full-time jobs and trying to break into the game the right way.If you’re a beginner feeling stuck, I’ve been there.

or simple break down deducting from security deposit totalTIA.  

Management and cleanings are key to success, either can make or break your income.

.🏡 BackgroundMy parents own a home currently worth $2 million, bought for $500KThere’s still a mortgage on it, but they have ~$1.8+ in equityMy goal is to partner with my family and responsibly borrow against the house to start building a rental portfolioI live at home, have almost no expenses, and want to reinvest aggressively💡 The Core StrategyFinish college with minimal debtLand a solid W-2 or commission-based job out of school (sales/consulting/real estate)Convince my parents to give me partial ownership of the house or structure a joint borrowing arrangementTake out an initial $300K–$600K loan against the home (not the full $1M+ possible)Use 25% down strategy to control $1.2M–$2M of real estateBuy 3–6 rental properties in cash-flowing marketsHold ~$50K–$100K in reserves to avoid overleveragingRent pays off all property debt + covers most (if not all) of the home loanUse job income to fill any short-term gap (targeting break-even or net-positive cash flow by year 2)Reinvest profits + refinance gains into new properties every 12–24 monthsEventually scale to 10–20 doors, pay off the home loan, and build a family portfolio🧠 Long-Term VisionCreate a multi-generational wealth plan with my brothersBuild an LLC or family trust to manage propertiesUse smart leverage + cash flow to retire early or buy full freedomTeach my family how to compound togetherEventually pass on millions in property to our kids — no debt, just systemsWhy I’m PostingI don’t need hype — I want honest feedbackWhat would you improve?

Ideally, I was trying to sell the first and essentially break-even selling the second by utilizing the funds from the first for anything due at closing. 

Federal support is being cut dramatically as you see in the news, but services are not being cut.

Additionally, despite the houses being newly renovated, every month there were new expenses and something breaking, almost as if they want me to not cashflow.