@Sydney Willford,Welcome to the BP community.I would strongly recommend to anyone in you position to look into "househacking" a duplex. 

You can always tackle the upgrades later once cash flow and equity improve.

When I see that happening, I'll have to rethink my positioning in real estate.

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.)

Hopefully you have enough equity to sell and move on

It's exhausting but the sweat equity was created.

After those years, appreciation not equity accrual is the most critical factor to walking with $ in hand from a sale. 

@Alex Olsonyep. long + unreservedly positive = AI

what is your equity position, property specs/location & property type what market are you looking to enter