Millennial Ditches High Rent, Steps up to Landlording with Duplex in Eastie

By July 24, 2016 August 3rd, 2020 Blog, Resources

For my fellow millennial friends it feels like just yesterday we were living the dorm life. Fast forward a few years and now everywhere you turn people are talking about buying property.  While some are vetting their first condo in or around the city, others are taking a different approach and buying multi-family houses. That’s right, people in there twenties are becoming landlords in order to build home equity and offset their mortgage payments. Sounds crazy, I know. I mean, what the fig? Who is actually doing this?

As a Realtor®, specialized in working with first time home-buyers and investors, I’ve been privileged to work hand-in-hand with some forward thinking clients ready to ditch their high rent and step up to landlording.

Below is the official story about my savvy buyer and good friend Artie and our process for finding him a duplex in East Boston. (Tip: you can download a PDF version of his case study here).


At 26 years old, Artie B. decided it was time to buy his first piece of real estate. After mentally committing to home ownership he was looking for advice on how to take action and to navigate the process.

Like many recent grads, Artie had bounced around from rental to rental. As a tenant, he was paying a high monthly fee for less than ideal living accommodations. Enough was enough.

“I was sick of living like a college kid and thought it was time to get my own place. I’d been hearing about low interest rates and I felt like I had a window of opportunity and became really motivated to make an investment.” Artie reached out to Dana Bull, a local Realtor® who specializes in helping first time homebuyers.

Hearing about the many benefits of owning a multi-family and having rental income help to offset a mortgage, Artie was interested in purchasing a duplex. The plan was to make his first purchase a primary residence. By renting out one of the units, along with a bedroom in his own apartment, he could make a significant dent in the cost of home ownership. As a first step, Dana recommended a mortgage lender to pre-approve Artie for a loan and to explore financing.

“Talking to a lender helped to clarify the different financing options that were available to me. Getting pre-approved was actually a lot easier than I had anticipated. After a ten minute phone call, I had a good idea of what I could put down and what to expect for monthly payments.”


Once Artie had a firm grasp on his budget, Dana jumped right in by coordinating showings in the target areas. “We toured several places together at night and on the weekends and Dana gave me some great pointers and outlined the pros and cons of each property. To make sure I felt educated on all the potential strategies, we looked at a variety of properties in Malden, Chelsea and East Boston. These included some fixer uppers and even a few mixed-used buildings. It was really an eye-opening experience for me. I couldn’t believe the conditions of some of the buildings. Throughout the process, the advice that Dana provided was invaluable. She brought up things that I never would have considered or even thought to look for in a house.”

The first real contender was a recently updated two-family in East Boston’s Eagle Hill neighborhood. The house featured a small rental on the first floor and a two bedroom multi-level unit on top. Unlike many of the properties that they toured, this house was already vacant and had updated kitchens, baths, separate utilities, and a long list of recent capital improvements.

“Dana really understood my goals and lifestyle and helped create an investment strategy that would work for me. She was really excited about this property and thought it would be a good fit. I liked the house and could see myself there, but only if I could get a deal.” After doing some market research and knowing that it wasn’t a competitive situation, Artie worked with Dana to write up a “low-ball” offer. Unfortunately, the sellers came back higher than Artie was willing to pay at that time. The house hunt continued.

“Things were really busy at work, so Dana previewed some properties for me during the day and nixed them if they weren’t worth looking at. It was a huge time-saver.”

Next, Dana found an affordable off-market three-family and immediately scheduled a viewing. The location was solid and the numbers worked well. While the property required some TLC to get it up to better rental standards, it had potential. Soon after seeing the property, they submitted an offer. After some back and forth negotiation, they had an accepted offer. At first, Artie was enthusiastic about the property, but during the inspection some issues presented themselves.

“Dana recommended an inspector specializing in old homes who provided a very thorough walk through. During the inspection he uncovered some things that concerned me. There’s no doubt it could have been a good investment, but as a first-time buyer, I really didn’t want to get in over my head. Ultimately, I just had a bad feeling about things and decided to walk.”

At the same time, the spring market was starting to pick up. Another party had expressed interest in the renovated two-family in Eagle Hill and it had gone under agreement. “At this point, I was a bit disappointed that the three-family didn’t work out and that the other two-family was off the table. Going through the inspection was a good learning experience. At first glance, I thought the three-family would work, but then upon closer examination I started to think about how much time and money it really needed. While originally I loved the idea of putting sweat equity into a fixer upper, I realized that something turnkey was more practical and felt less risky for my first purchase.”


A few weeks went by and they continued their search. “We talked about other options, like condos and looked at some other two families, but I wanted to hold out for another renovated two-family like the Eagle Hill option. I kept going back to the first place and thinking that it was the one that got away.”

It was lucky Friday the 13th when Dana reached out to the listing agent of the Eagle Hill property and learned that it was coming back on the market due to a buyer financing issue. After relaying the good news to Artie, he was ready to jump in with two feet. “This time around, I knew exactly what I wanted and felt really confident about the decision. I saw everything that was out there and by going through the process with the other property, I understood why Dana thought this house would work for me in the first place. Sometimes you just need to come full circle.”

After submitting a serious offer and negotiating the terms, the seller accepted a price 10k under list. “Dana really pulled through in the negotiation. They were gearing up for an open house and she was able to lock it down before anyone else had the chance to see it.” Since the house was recently remodeled, they were hoping for no surprises. The inspection was clean until the very end when a potential structural issue was discovered.

“Dana really went above and beyond. She looked through the city permits to see who had done the work at the house and she was able to get the same general contractor in to explain the issue. He was able to clear up my concerns and provide the answers I needed to move forward.”

Artie then partnered with his lender to hammer out the financing details and enlisted a real-estate lawyer to organize the necessary closing documents.

“It was obvious that the team had a lot of experience working together. Things were going on behind the scenes to ensure a smooth close. They got it done with few distractions or stress on my end.”


After closing on the property, Artie quickly prepped the unit for tenants and consulted with Dana on how to find renters.

“While Dana could have rented out my apartment for me, she thought it was important that I had control. Dana shared tips on how to market the apartment and walked me through some ways to screen tenants. I actually found someone to fill the vacancy right away and they moved in the weekend after I closed.”

Not only was Artie stepping up to home ownership, he was also stepping up to landlording. Becoming a landlord is no small feat and it requires strong organization and people skills. It’s not for the faint of heart. Fortunately, Artie’s fast paced office job prepared him well for the demands of becoming a landlord.

Now he’s all moved into the duplex and enjoying the rent-free lifestyle. So far, there have been no major issues. While things will crop up over the years to come, Artie will take them in stride knowing that this is a long-term investment strategy.

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