At some point, the biggest learning jump comes from underwriting real deals and talking to lenders, agents, and property managers.For a duplex or triplex house hack, I’d focus less on “financial freedom” narratives and more on execution basics: conservative underwriting, realistic rehab/maintenance assumptions, and making sure the numbers work even if things don’t go perfectly.The goal of the first deal isn’t optimization, it’s getting through one full cycle cleanly so you can repeat it with confidence.Best of luck!

The reason we still feel bullish (not reckless) is that there are several obvious levers the prior operation didn’t really pull: delivery/pickup was not executed well; we’re partnering with owner.com to rebuild the website/app funnel and online presentation (not a plug — just something we believe will move the needle),delivery radius will be supported via Uber drivers (~15 miles),alcohol sales were only 1–3% previously because the old location didn’t have an actual bar and there was basically no signal that they served alcohol (no mixed drinks, no “bar energy”),the new space has a fully remodeled (2007) kitchen/dining, plus a legit outdoor eating area, and we’re reopening there in April.  

I’m learning real estate investing and interested in property research, rental comps, and basic deal analysis.

Staffing, maintenance, seasonality, and guest management are all very real challenges, particularly on the East Coast where you shut down and basically have to rebuild the team every spring. 

That’s a great example of how “by-right” on paper doesn’t translate cleanly into a buildable or financeable outcome.I see the layout issue you’re describing come up a lot on constrained infill sites—especially when max unit counts drive land value before basic test fits or parking realities are fully thought through.

I think I'll try the throwing hot water into the air trick.

Basically structure a deal where the seller gets 70% from my lender and I finance the 30% with the seller. 

Don’t let that number push you into overconfidence early.If this were me at 21, I’d prioritize:• A conservative house hack that cash-flows or breaks even• Learning tenant screening and maintenance basics firsthand• Preserving flexibility for deal #2, not maxing leverage on deal #1There’s no rush.

I would select a market which has strong rental demand and affordable entry costs like TX, then I would calculate basic deal metrics which include cash on cash return and monthly cash flow before I start my advanced analysis.

As to the complications of owning/investing overseas, it's not easy to answer general questions but basically depends on the country.