Narrowing Down a Market

[Luke Wininger]

Hi Everyone,

My name is Luke and I'm a rookie investor looking for my first deal. I'm located in Central Connecticut, have saved about $50k for real estate investing, and have decided that I would like to house hack a multifamily to get into my first property. I want to buy within about a 30 minute radius of Hartford, but not necessarily in Hartford itself. I'm curious what towns have worked well for others who have used this strategy. It seems like towns with the most inventory of multifamily homes have lower price points and property taxes, but may not appreciate as much compared to higher income towns like West Hartford and Wethersfield where the prices are higher but there is greater upside for appreciation. 

Do I focus on finding properties in nicer neighborhoods within the lower income towns? Do I wait for more assets to hit the market in higher income towns?  Do you think appreciation or cashflow is more important for a first investment?

I'm open to recommendations on towns/areas to look into and I'd love to connect with other local investors who are willing to share their experience. 

I appreciate your help in advance!

- Luke Wininger

[Pavel Voroniuk]

This is a really common tension to be thinking through for a first house hack. The way I’ve been approaching it is by underwriting markets the same way I underwrite individual deals — looking at taxes, rent-to-price relationships, tenant demand, and how forgiving the area feels if assumptions don’t play out perfectly.

Around the Hartford area, the trade-off you’re describing shows up pretty clearly: lower-priced towns often pencil better on day one but can come with more operational friction, while higher-income towns tend to feel more durable long term but are harder to make work initially. For a first house hack, I’ve found it helpful to prioritize downside protection and livability over trying to optimize appreciation right away.

Underwriting a few properties across different towns using conservative assumptions and asking which market you’d feel most comfortable holding through a slow year or two has helped me narrow things faster than trying to predict which area will appreciate the most.