2015 saw the acquisition of a second two family property in Medford, MA, which I worked with my father to BRRR. We bought at $510,000, had it re-appraised for $870,000 a few years later, and we were able to take funds out and buy another two unit off market through a contact I had made in the rental business (more on that in 2020).

At this point in time, the power of real estate investing was abundantly clear to me and I dedicated myself to acquiring more properties and started devouring educational content.

I acquired another property in East Boston, a blossoming area just outside the city center. This two-family was a quick, 5 minute walk to a subway stop and only about 15 minutes via public transit to Logan International Airport. This property had one unit that was rental ready and another that needed a significant rehab. With one unit rented, I was able to have work done on the other, which minimized holding costs during the renovation. Once finished, this property was my first foray into the short-term rental space (plenty of interesting stories about that) as I had one unit on Airbnb and the other long term rented (wouldn’t recommend this approach, btw!). The short term rentals proved to be extremely lucrative as the location was very advantageous, but I decided to sell this property in late 2020 as it had appreciated quite a bit with the renovations and general market trends.

At the sale, I was able to realize an ~$80,000 after tax gain on this long term flip project which I used to purchase other investments down the line.

Realizing success from my initial STR experience with the East Boston project, I dove into another STR project with the purchase of a small two family in Revere - a town just outside Boston city limits with walking access to the subway AND the beach! This house was on the market for a while since it’s extremely unique - it’s a tall, skinny structure in the shape of a lighthouse. I feel that most investors were looking at this as a long term rental, which is a hard sell due to its unique unit layouts. However, this is exactly what I was looking for as a short term rental - unique features, updated units, easy city and beach access, parking, water views, just to name a few. My vision proved right as this property consistently brings in 3-5x what long term rents would be for the area and is our top performing STR investment to date, despite recent turbulence in the STR market (full video on that here).

At the end of 2020, I had a rare opportunity to purchase an off market two family property on the Cambridge line in Watertown, MA. This is an extremely desirable area close to Boston proper and Harvard Square, so I knew it was something I couldn't pass up. It came from a relationship I made in the rental business and proves how invaluable connections are in real estate investing. Together with my father, we were able to purchase the property with refinanced funds from our 2015 project. The house is made up of two, side-by-side townhouse units and we renovated both to near condo quality to capitalize on a higher end rental market in this area. Bought at $965,000, this property would appraise for north of $1.3M today and cash flows extremely well for the area. Considering the strong rental market and high appreciation, this property is a surefire long term hold which we continue to reinvest in to maximize rents.

Additionally, we acquired a fully renovated two family in a very nice town just north of Boston where we reside today. This property has a huge one bedroom on the first floor and a massive four bedroom/two bath upstairs. At the outset, we lived in the one bedroom with the other covering the mortgage, but have since moved to the larger one with the smaller paying about 75% of our mortgage. I’ve always been a dedicated fan of house hacking for this reason and preach it as one of the best entry points for new investors. Coincidentally, this was right before rates spiked and was one of the last chances to find investments like this in the Boston area, so we’re glad we acted when we did.

2021 was a period of massive growth for our portfolio as my wife came over full time to scale up our short term rental business. Using funds from previous refinances, we were able to acquire six new units - two in the town of Manchester, VT and four in Bethlehem, a town just outside of Littleton, NH. We invested a lot of time into automating the Airbnb process as much as possible and built our systems out significantly to ensure a smooth and efficient rental process. We entered this phase at the absolute height of Airbnb earnings during Covid, but have since experienced some downward market trends. We now employ a mix of long, mid, and short term rental tactics and both these properties continue to perform very well despite market volatility. If you’d like to check out our NH property and learn more about that, you can do so here.

The fourth unit at our NH property is a standalone cottage behind the main building. We loved this deal because the cottage was included, representing significant value-add. The only issue was that the cottage needed a complete gut renovation (I mean EVERYTHING), so it would be the first time I undertook that scope of renovation, that far from home (2 hours). Long story short, some mistakes were made managing contractors and we ended up nearly doubling our budget, but there was so much upside to this project we still netted out a 20%+ ROI (man, real estate is forgiving!). See all the details on this in my YouTube video here.

After our recent rehab project, it became clear that the subject property was much better suited to two parcels instead of just one. The lot was unique in the way that it abutted two roads which made it prime to subdivide.

The only issue was the proposed plots were non conforming in terms of size and frontage, so it required a variance. Working with a surveyor, I successfully petitioned the town to have the subdivision approved, essentially creating a new single family lot and dwelling that can now be sold or refinanced.

With the market essentially frozen since 2022 (high rates, low inventory), this felt great to figure out a different way to add value. Investors in the current market need to be extremely creative and patient to make deals work, but it can still be done!