Six properties.
One Rochester street.

Mark Updegraff purchased his first Gregory Street property in 2008. Over the next five years, he returned to the same South Wedge corridor for five additional acquisitions: five single-family houses and one two-family property, creating a six-property, seven-unit concentration.

The portfolio was not assembled through one package purchase or a single financing event. It grew through repeated acquisitions, renovations, leasing, refinancing decisions, and long-term ownership. The strategy followed the principles now commonly described as BRRRR: buy, rehabilitate, rent, refinance, and repeat.

How Gregory Street started it all

After reading Rich Dad Poor Dad, Mark decided to take a leap of faith despite people around him saying the purchase was crazy. His first investment was a house on Gregory Street in Rochester's South Wedge—a neighborhood that, in 2008, still had visible blight and regular concerns about crime.

The previous owner had kept knives within reach throughout the house. When Mark collected them after closing, they filled a bucket—an unforgettable picture of how vulnerable she had felt in the property. He completed the rehabilitation himself, put the house into service, and immediately began looking for the next project.

His second acquisition was elsewhere and did not perform as well, but it gave him a useful benchmark. Meanwhile, the Tap and Mallet opened two doors from the first Gregory Street property. The arrival of a popular neighborhood pub reinforced what Mark was beginning to see: Gregory Street's distressed housing stock sat inside a neighborhood with real momentum.

The later Gregory acquisitions arrived one at a time and in very different ways. Mark bought one distressed property from an older investor who remains a friend today, acquired another through foreclosure, and took on a building so damaged that it spent years on the back burner as the “Troll House.” Before that house could be fully renovated and returned to service, it even became a public haunted house for one memorable season.

Why concentrate on one street?

Concentrated ownership can create advantages that do not appear in a conventional property spreadsheet. Repeated work in the same few blocks improves the owner's understanding of housing stock, buyer and tenant demand, renovation patterns, rents, comparable sales, and recurring maintenance issues.

• Faster pattern recognition. Similar construction eras and property types make it easier to recognize recurring systems, defects, and renovation needs.
• Better operating context. Leasing activity, resident experience, maintenance calls, and turnover provide direct evidence about demand at the block level.
• More efficient field operations. Nearby properties reduce travel and make inspections, service coordination, and project oversight more practical.
• Visible accountability. Concentration increases the owner's stake in how the immediate street performs over time.

What the BRRRR acronym leaves out

The five-letter formula makes the strategy sound linear. In practice, the difficult work happens between the letters. A purchase has to survive a realistic renovation scope. The finished property has to meet actual tenant demand. Operations have to support the debt. A refinance has to work under the lender's valuation, seasoning, income, and documentation requirements at that time.

Repetition helped sharpen the questions Mark now brings to Rochester investment-property decisions:

1. Is the basis low enough to absorb the work the property truly needs?
2. Which improvements affect safety, durability, rentability, and long-term value?
3. Are projected rents supported by the specific block and unit—not merely a citywide average?
4. What operating expenses and capital needs remain after renovation?
5. Does the property still work if the refinance, lease-up, or exit takes longer than expected?

Lessons from long-term ownership

Neighborhood knowledge compounds

Market reports are useful, but ownership creates a different type of evidence. Years of leasing, maintenance, renovation, and resale activity reveal differences that broad statistics can miss. In Rochester, two properties with similar layouts can produce very different outcomes because of condition, utilities, taxes, resident demand, and their precise location.

Renovation is only the beginning

A successful rehabilitation may create a better physical asset, but long-term performance still depends on leasing, collections, maintenance, reserves, insurance, taxes, and management. The owner has to operate what the investor underwrote.

Repeatable does not mean identical

The approach became more informed with each acquisition, but the properties did not share a single formula. The practical discipline was to reuse good processes while continuing to underwrite each building on its own facts.

Concentration creates responsibility

Owning multiple properties on the same street makes the connection between individual decisions and neighborhood conditions harder to ignore. Exterior maintenance, resident experience, construction quality, and responsiveness are not abstract portfolio metrics; they affect the same place repeatedly.

How the experience informs client work

The Gregory Street portfolio is one reason Mark evaluates Rochester investment property from more than a transaction perspective. Buyers need to understand the building they may have to renovate and operate. Sellers need to know which records, operating facts, and improvements matter to qualified investors. Owners weighing management or disposition need advice grounded in what happens after closing.

That experience now connects three related perspectives:

• Updegraff Group Realty — acquisition, valuation, positioning, negotiation, and disposition.
• Updegraff Management — leasing, maintenance coordination, resident service, and property operations.
• Mark's Gregory Street discussion on BiggerPockets — his firsthand account of the first purchase, the renovations, and the neighborhood's evolution.