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.)

I love this, we recently bought a fixer up that had 5 adjacent lots that we will build on eventually. 

Be the guy that eventually, the business can't do without and you'll have more opportunity than resources in short order. 

You will want to avoid the towns with wacky lawsLong term rental is great but I will let you know  I am in the process of converting a LTR of mine to mind term rental taking rents from $3k to over $5k so I always suggest to clients, be open mind to MTR especially if you want cash flow on day 1value add is great, really one of the fastest ways to leverage property 1 to purchase property number 2. 

If you eventually want to take a position of selling you will owe taxes on what you depreciated. 1031 is always an option but this piece was laid out for those that are not in a position to roll funds into another property but simple want to "cash out"Appreciate you mentioning ChatGPT.

My wife spent hours on the phone with Buildium customer service and kept getting bounced around to different people, but eventually ended up on the phone with the 3rd party company Buildium uses to run their backgrounds.

However, all markets that eventually work, must be accompanied with the proper strategy. 

So if both sides are about the same size, roughly half of your gain could be deferred, and the other half would be taxable since it’s for personal use.Later on, if you hold the property for a while and eventually convert the whole thing to your primary home, you might be able to combine the 1031 rules with the home sale exclusion under Section 121, but that takes careful timing and planning.It’s definitely worth mapping out before you sell so you don’t miss any opportunities.

We’re located in Westchester County, NY, and our goal is to eventually get approved for more so we can purchase a house to house-hack (ideally a small multi-family).

These strategies will allow me to build some capital and experience, eventually partnering with other investors to own properties and generate true passive income.If anyone is willing to help — whether through wholesaling, bird-dogging, or even partnering with me on my first deal — I would be incredibly grateful.