The Journey

Back in December 2020, my girlfriend Annie and I started taking the steps needed to become homeowners. After getting pre-approved, we started looking into single-family homes in Connecticut, but shortly after realized that we couldn’t afford it comfortably if we wanted to eat every day. After some bumps in the road, learning the ins and outs of the home buying process, and keeping our options open – we were able to close on our first home on June 1, 2021.

The Wake-Up Call

There were slim pickings on the market for single-family houses – seriously, it was bad! Small 1-2 bedrooms that were not in the best shape were the most affordable option.

I spent months disappointed in the housing market and kept asking myself, “how can anyone afford this?” and “is there a smarter way to do this?”

I’m 25 years old and make less than 50K a year. I’ve never owned a home or started a business, but I know how to research and fall down YouTube rabbit holes to get the information I needed.

I read Robert Kiyosaki‘s book, Rich Dad Poor Dad – which sparked my interest in real estate investing and the idea of building passive income to achieve financial freedom. After reading the book, I signed up for a few webinars where I learned about house hacking.

We shifted our perspective – instead of stressing to find an affordable home, we started running numbers and viewing it as a business investment.

The Search

We knew we wanted to go the investment property route – we’d purchase a multi-family property and live in one of the units while renting out the others. This was to help offset the cost of the monthly mortgage payment and start building passive income in the process.

I ran numbers on all the affordable duplexes and triplexes in my area and came down to four reasonably priced properties. I booked showings for all of them in one day – which I 10/10 don’t recommend doing. I was exhausted driving from Wilton to Naugatuck, Naugatuck to Milford, and then shooting over to Norwalk and then back to Wilton.

All but one of the properties I viewed were duplexes and there was one 4–plex. The 4-plex in Naugatuck was the only property we saw that had potential. The units were well-maintained and fully occupied for over ten years. The building itself was built in 1852 – at most, it required some updates to modernize it. We put in an offer, and it was accepted!

The Inspection

If I learned anything in my research, it was about the value of a home inspection. I hired Chris Girlamo from Revere Inspection, LLC to get a better picture of the work we would need to do on the property.

The inspector did a general property inspection, tested for lead and termites, checked the roofing, HVAC, plumbing, and electrical systems.

Overall, the property was in great condition, but it did have three sets of exterior stairs that were unsafe and out of code. Our realtor Patrick Blois negotiated with the seller to have a credit of $9,500 issued to repair the stairs.

Aside from that and a few dead trees on the property that we needed to remove, we just needed to figure out whether or not there was an oil tank underground. The seller had no knowledge of an underground oil tank, so we had to hire an oil tank inspector to scan the ground.

Our biggest fear was the inspector finding an oil tank underground because it would be costly and could even lead to environmental issues since there is a creek to the right of the property.

Thankfully, there was no oil tank found under the property, and from that point on, everything else was smooth sailing.


We closed on our home on June 1, 2021. The home closing wasn’t the end of this journey, but it was the start of something new. We spent the first two weeks caulking, painting, and redoing the flooring in our unit. The apartment is almost done, we need to finish updating the bathroom and kitchen, but we’re on track to finish everything by the end of September! Once our unit is done we’ll do some minor updates on the other 3 units.

Despite the ups and downs of stress and anxiety throughout the home buying process, I’m happy we took the route we did. Not only are my partner and I homeowners, but we’re also investors who have great tenants and are only paying $200, before increasing rent, between both of us for our mortgage.

This process showed me that buying a home as a millennial is realistic. If you don’t make a significant annual income and aren’t afraid of giving a property a little TLC love, house hacking is a great way to achieve homeowner status!

Before vs. After Gallery:

Unit #4

Living Room









Bedroom #1






Bedroom #2





Exterior Stairs

Stair Case #1


**We decided to change the direction of the stairs to avoid getting hit on the gutter when going up.**

Stair Case #2


Stair Case #3


Still in progress:


Stairs/ Upstairs Hallway




Who we worked with: 

Realtor – Patrick Blois

Home Inspector – Chris Girlamo – (203) 273-1167

Electrician – John Balzano Electric (203) 910-9139

Plumber – Vinny Costello – (203) 206-8597

Carpenter – Erik Jacobson – (203) 592-4242

Windows – Jay Craig/ Anderson Renewal – (203) 243-3209