$120,000/Year Cash Flow with 9 Rentals by Buying What TENANTS Want

TL;DR

Greg Roersimer built a $120K/year cash-flowing portfolio of 9 paid-off rentals by targeting scarce single-family ranchers that tenants in Richmond, Virginia actually want.

Key Points

• 1.Greg became an accidental landlord in 2007 after buying at the peak. He purchased his first home in Harrisburg, PA just before the crash, found it worth less than he paid, and was forced to rent it out when he relocated to Richmond, VA with his wife.
• 2.He returned to real estate in 2021 after a 14-year gap, motivated by a corporate midlife crisis. Greg and a work colleague asked themselves whether they wanted to work in an office until 65; his dad retiring at 52 was his financial independence model.
• 3.His first investment was a turnkey condo bought for $172,500 with a 50/50 partner, cash-flowing $500/month. The tenant had been paying $1,100 for 10 years; they raised rent to $1,500, used a commercial loan, and each put in $25,000 sourced from Greg's consulting side hustle.
• 4.Greg identified demand for single-family ranchers by simply driving around Richmond. New construction was either too expensive or lacked land; one-level homes also appealed to older tenants needing accessibility, and this insight drove his core buy box.
• 5.His first single-family rancher cost $245,000, rented for $1,600 immediately, and now fetches $2,200 — a 37% rent increase in four years. Properties built in the late 1970s through early 1990s with carrying costs around $1,200 form the backbone of his portfolio.
• 6.When rates rose in 2023, Greg shifted to paying cash to buy wholesale and as-is MLS deals under $250K. One wholesale deal cost $240K plus $40K in rehab, rents for $1,900, and is now worth $320K; an MLS as-is deal at $255K all-in ($290K after repairs) became his first BRRRR via a cash-out refinance.
• 7.Greg partnered with his contractor on a $180K wholesale deal, splitting capital vs. labor 50/50. The project ran nine months instead of six and cost $100K in renovations; Greg ultimately bought out his partner and kept the property, then continued buying two more deals together through the same wholesaler.
• 8.Nine paid-off properties — two condos and seven single-family homes — generate roughly $120,000 in annual cash flow. Greg self-manages all properties within a 25-minute drive, plans to employ his kids for tax benefits, and credits buying what tenants want over chasing the cheapest possible asset.