But we can essentially create cashflow by creating paper losses.

Remember avoid making the layout odd by trying to cram in an additional bedroom.

You're forcing numbers to make a difficult deal appear doable on paper.

.• You cap the loss once• You free up capital and bandwidth• You avoid 10 years of hoping the math fixes itselfMany investors underestimate how powerful not carrying a bad deal can be.Option 3: Improve economics without refiBefore injecting $30–40k, explore:• Roommate or mid-term rental strategy (if HOA allows)• Employer-backed or furnished rentals• House-hack style repositioning if layout allowsThese are operational fixes, not financial ones, but sometimes they bridge the gap.The biggest mistake to avoidHolding purely because “it should appreciate” while ignoring opportunity cost.

Strong returns on paper don’t always justify high operational drag.

I can tell by this if it's the specific location or design/layout or condition that's driving demand.I can then take what I learn through that reconnaissance and pair it with the data sets available online to form a more informed view of the neighborhood’s trajectory.

Floorplan/layout.

Usually these are properties with paper equity that never translates at time of sale.

One change order turns into three, then you are waiting on a cabinet layout, then counters, then the whole schedule slides.

Time is your biggest advantage right now.A few high-level points first:• Two years of runway is plenty• House hacking is the right instinct• Starting with secured credit is fine, you’re early• You do not need to rush into anything fancyNow to your questions.What type of property to focus onFor a first deal, especially a house hack, keep it boring and finance-friendly:• 2–4 unit small multifamily (duplex, triplex, fourplex)• Simple layouts, similar unit sizes• Something that qualifies for owner-occupied financing (FHA or conventional)This gives you:• Low down payment• Rental income offsetting your housing cost• A built-in learning experienceSingle-family can work, but small multifamily teaches you faster.Chicago-specific thinking (general, not neighborhood calls)Instead of asking “good vs bad areas,” focus on:• Areas with stable rents, not speculative appreciation• Neighborhoods where duplexes and small multis are common• Places with working-class demand and long-term rentersAvoid:• Heavy rehab projects for your first deal• Areas that only work if appreciation bails you out• Deals that rely on perfect executionYou want boring and durable, not exciting.LLC for your first purchaseShort answer: no, not for your first house hack.• Buy in your personal name• Use owner-occupied financing• Get the best rate and lowest down paymentYou can always move properties into an LLC later once you scale.