The days prior to Covid almost seem a lifetime away. In the fall of 2018 my girlfriend at the time and now wife were in the market for our first place. We had been looking for months being outbid by every other new home buyer and downsizer also in desperate search for a roof and four walls.

Luckily enough, by 2019 we were home owners. A tired townhouse in a wonderful community just off one of the largest commuter highways in New Hampshire. Little did we know, scraping together $18,000 for the down payment, closing cost and miscellaneous would help us build a $2,000,000 Real Estate portfolio in just five years.

In today's blog, we will explore how we took our first down payment on a condo and turned it into a Two Million Dollar portfolio in just five year. Let's explore the five key factors of each deal - 

Deal #1 - The TownHouse 

How We Found the Deal - Word of Mouth (Off Market Deal)

How We Financed the Property - FHA Loan (5% Down w/ PMI)

Renovation Cost on the Property - $18,500

How Long We Held the Property - 2.1 Years (Tax Free Gains - Section 121 Exclusion)

What We Did With the Proceeds - Bought Deal #2 and Deal #3

Commentary - This was our first live in flip. Small projects ranged from LVP Floors, Paint, Windows, Deck Work, Basement Facelift and Carpet Replacement

Deal #2 - The Two Family 

How We Found the Deal - MLS (Search: DOM of 180+ Days)

How We Financed the Property - FHA Loan (5% Down w/ PMI)

Renovation Cost on the Property - $21,000

How Long We Held the Property - 2.2 Years (Partial Tax Free Gains - Section 121 Exclusion)

What We Did With the Proceeds - Bought Deal #5

Commentary - This was our first go at being landlords and I am glad we started small. We learned how to act fast when maintenance is needed. Learned what should and should not be in a lease through trial and error and started to build systems for future automation.

Deal #3 - The Single Family Flip

How We Found the Deal - Word of Mouth (Off Market Deal)

How We Financed the Property - Private Money (10% Down)

Renovation Cost on the Property - $74,000

How Long We Held the Property - 0.6 Years

What We Did With the Proceeds - Bought Deal #4

Commentary - Although we got a great deal, every inch of this house was filled with junk. A hoarder home special. This was our biggest undertaking to date at taught us a lot about project management from budgeting to juggling contractors. 

Deal #4 - “The Salon” A Five Unit Mixed Use Building

How We Found the Deal - Zillow (Search: DOM of 90+ Days)

How We Financed the Property - Private Money (10% Down)

Renovation Cost on the Property - $110,000

How Long We Held the Property - 2.6 Years (Still Under Management as of 07/2026)

What We Did With the Refinance Proceeds - Bought Deal #5

Commentary - This was our first step into Commercial Real Estate and what a good choice it was. This building in particular has been a challenge but has taught us so much about the permitting process and navigating town hall that we felt comfortable enough to do it again.

Deal #5 - “The Restaurant" A Five Unit Mixed Use Building

How We Found the Deal - Cold Called Owner (Restaurant Closed)

How We Financed the Property - Seller Finance (10% Down)

Renovation Cost on the Property - $195,000

How Long We Held the Property - 1.2 Years (Still Under Management as of 07/2026)

What We Did With the Refinance Proceeds - Bought Deal #6

Commentary - This is likely our pride and joy. A roughly $200,000 renovation that we were able to complete in just nine months. Now a fully occupied five unit that generates a smidge over $10,000 a month in Revenue.

Deal #6 - “The CareTakers Unit” A Commercial Building and 1,600 sq ft CareTakers Unit

How We Found the Deal - Seller of Deal #5 

How We Financed the Property - Seller Finance (10% Down)

Current Renovation Cost - $105,000 (As of 07/2026) 

Estimated Renovation Cost at Completion: $155,000

How Long We Held the Property - 0.8 Years (Still Under Management as of 07/2026)

What We Did With the Refinance Proceeds - TBD

Commentary - This deal fell into our lap. After making good on the Restaurant renovation, the prior owner approached us to see if we had any interest in the building next door to it. We did! We got such a good deal that we chose to get permission from the town to add a caretakers unit which Brittany and I just moved into this summer.

Yes, each of these deals has led to an increase in financial wealth but more importantly, a genuine increase in all things Real Estate knowledge. 

I believe that every real investor should start small and grow as they develop a strong base in the following three areas - 

Today's blog may not have gone into a lot of depth but I believe it is still important to share where we started and how we got to where we are today. We self manage deals #4,5 and 6 above still and continue to have our fair share of good days and bad days as we continue to learn and grow.

Every blog written stems from these 6 deals and I hope to continue to share more and more details about our journey are Deals #7,8 and 9 come together in time.