Here’s the listing:--> https://www.zillow.com/homedetails/398-402-Boston-Post-Rd-Wa... price: $350,000My plan:Live in the smaller homeRent the larger home immediately (after light cosmetic work)Use FHA (3.5% down) + CHFA (down payment assistance)Reduce my personal housing cost as much as possibleSlowly fix my unit over timeBuild equity and eventually refinance to help fund a future businessNUMBERSPurchase Price Target:Offer target: $260,000Expected seller counter: $275,000–$300,000Currently listed at: $350,000FINANCING (FHA + CHFA)FHA 3.5% downDown payment covered by CHFA assistance programEstimated interest rate: ~6.5–7%MONTHLY PAYMENT ESTIMATES (P&I + Taxes + Insurance)At $275,000 purchase:Mortgage (P&I): ~$1,775Taxes: ~$420Insurance: ~$150--> Estimated Total: ~$2,350/monthAt $300,000 purchase:Mortgage (P&I): ~$1,940Taxes: ~$420Insurance: ~$150--> Estimated Total: ~$2,510/monthRENTAL INCOME ESTIMATE (Big House)Based on local comps:Low: $1,700/monthTypical: $1,800–$1,950/monthStrong (clean/paint/update): $2,000–$2,100/monthMY OUT-OF-POCKET HOUSING COST AFTER RENTIf I rent the big house at $1,900/month:At $275k: ~$450/monthAt $300k: ~$610/monthIf I rent at $2,000/month:At $275k: ~$350/monthAt $300k: ~$510/month(I currently pay $0 in rent living with family, so my goal is to keep my costs low while building equity.)REHAB ESTIMATESBig House (rent-ready):Cleaning + paint + small fixes: $1,000–$3,500Optional cosmetic upgrades: $2,000–$5,000Small House (my unit):Cosmetic repairs only: $500–$3,000Optional improvements (done slowly): $2,000–$7,000Major systems (worst-case ranges):Roof: $8k–$12kBoiler: $4k–$8kElectrical panel: $1,500–$4,000Plumbing repairs: $500–$2,000 typical(Inspection will tell me more.)CASH NEEDED TO CLOSEWith CHFA:Down payment: $0 out of pocketClosing costs: varies, but often reducedExpected out-of-pocket: $1,400–$1,800Inspection: $400–$600Appraisal: $500–$700MY FINANCIAL POSITION(To give you context for risk tolerance)Income: $5,000–$6,000/monthMonthly bills: ~$2,600Emergency fund: $10,000Credit: 717Access to 0% APR business credit card (likely $8k–$12k limit)Currently pay $0 rent (living with family)MY QUESTIONS FOR THE COMMUNITY1.)

Here’s the listing:--> https://www.zillow.com/homedetails/398-402-Boston-Post-Rd-Wa... price: $350,000My plan:Live in the smaller homeRent the larger home immediately (after light cosmetic work)Use FHA (3.5% down) + CHFA (down payment assistance)Reduce my personal housing cost as much as possibleSlowly fix my unit over timeBuild equity and eventually refinance to help fund a future businessNUMBERSPurchase Price Target:Offer target: $260,000Expected seller counter: $275,000–$300,000Currently listed at: $350,000FINANCING (FHA + CHFA)FHA 3.5% downDown payment covered by CHFA assistance programEstimated interest rate: ~6.5–7%MONTHLY PAYMENT ESTIMATES (P&I + Taxes + Insurance)At $275,000 purchase:Mortgage (P&I): ~$1,775Taxes: ~$420Insurance: ~$150--> Estimated Total: ~$2,350/monthAt $300,000 purchase:Mortgage (P&I): ~$1,940Taxes: ~$420Insurance: ~$150--> Estimated Total: ~$2,510/monthRENTAL INCOME ESTIMATE (Big House)Based on local comps:Low: $1,700/monthTypical: $1,800–$1,950/monthStrong (clean/paint/update): $2,000–$2,100/monthMY OUT-OF-POCKET HOUSING COST AFTER RENTIf I rent the big house at $1,900/month:At $275k: ~$450/monthAt $300k: ~$610/monthIf I rent at $2,000/month:At $275k: ~$350/monthAt $300k: ~$510/month(I currently pay $0 in rent living with family, so my goal is to keep my costs low while building equity.)REHAB ESTIMATESBig House (rent-ready):Cleaning + paint + small fixes: $1,000–$3,500Optional cosmetic upgrades: $2,000–$5,000Small House (my unit):Cosmetic repairs only: $500–$3,000Optional improvements (done slowly): $2,000–$7,000Major systems (worst-case ranges):Roof: $8k–$12kBoiler: $4k–$8kElectrical panel: $1,500–$4,000Plumbing repairs: $500–$2,000 typical(Inspection will tell me more.)CASH NEEDED TO CLOSEWith CHFA:Down payment: $0 out of pocketClosing costs: varies, but often reducedExpected out-of-pocket: $1,400–$1,800Inspection: $400–$600Appraisal: $500–$700MY FINANCIAL POSITION(To give you context for risk tolerance)Income: $5,000–$6,000/monthMonthly bills: ~$2,600Emergency fund: $10,000Credit: 717Access to 0% APR business credit card (likely $8k–$12k limit)Currently pay $0 rent (living with family)MY QUESTIONS FOR THE COMMUNITY1.)

It helps keep liquidity free for repairs or operating reserves while still allowing you to move quickly on a deal.

If you wait to use the VA loan, you could do this with no money down, live in the property for a year, and still write off the rental portion (repairs, interest, depreciation).

Flips can make it tougher for some buyers, but they also take homes most families can’t finance or repair and turn them into something safe and move-in ready.

With a property this old and with the issues you’ve already identified, the lender may require certain repairs to be included in the rehab portion of the loan rather than letting you handle them afterward with your own funds.The active roof leak and the wall sinking from possible settling are both items that typically will not pass underwriting unless they’re formally added to the renovation budget.

Two quick tips: sanity‑check those rent and expense assumptions with a local PM, and run your numbers with a conservative vacancy/repairs line so the cash flow is real, not rosy.Which neighborhoods are you targeting locally, and do you have a PM you can call this week to verify rent and expenses for that duplex/triplex/fourplex range?

I’d recommend learning how to accurately estimate rehab costs, study local ARVs (After Repair Values), and build relationships with reliable contractors and agents who understand investment properties.

Review Capital ExpendituresEnsure large repairs and improvements are logged correctly.

Learn your numbers before you learn your scripts.If you can estimate ARV and repairs confidently, sellers take you seriously and buyers trust your deal.