Rookie looking where to begin ?

Question

I live in New York but I’m looking to start investing in real estate out of state. The NY market is just so expensive that it feels hard to get started here. Starting in August I'm gonna be doing business in The Southern Massachusetts area.

From listening to podcasts and doing some research, Hartford, CT seems like a hot market for investors. I’m interested in possibly buying a duplex or a single-family home as a rental. I currently have about $100k that I’m looking to invest and my goal would be to make my first purchase sometime by this fall.

That said, investing out of state feels a little daunting. For those of you who have done it, where do you begin? How did you build your team (realtor, property manager, contractor) in a market where you don’t live?

Also curious if Hartford is still considered a good market or if there are other nearby cities in the Northeast that investors are targeting.

Any advice from people who have gone through this process would be really appreciated.

Kerlous Tadres · Answer

@Thomas Corrar, When you’re buying out of state, you want to check three things before you even look at listings: what similar places actually rent for (not what landlords “ask”), what taxes/insurance run on real deals, and how fast good property managers can place and keep solid tenants. If those three pencil out conservatively, the rest is just building the team and sticking to your numbers.

Daniel McDonald · Answer

I grew up about 20 minutes away from Hartford, and I definitely find it ironic that everyone is pushing Hartford and Springfield, MA. Both areas have definitely gotten a lot better, and probably (hopefully) will continue to, but they still have some pretty rough parts. I'm not surprised that both get a lot of investor attention because prices are still relatively fair, but I wouldn't recommend solely focusing on a cheap OOS market, especially if this is your first investment. Can you house hack in your area? Trust me, I felt pretty similar. I live just outside of Boston, which is brutal for pricing, but the 100k I spent towards house hacking acquired assets that have appreciated substantially faster than the C-class properties would have. That being said, I also manage properties out of state, and it's DEFINITELY doable, it just all depends on your risk tolerance. If you do want to explore Hartford, I would be happy to recommend an Agent. Feel free to reach out.

Bruce Woodruff · Answer

If you're going OOS, ,maybe pick an area that you might enjoy visiting, especially if you think you might ever do an STR....?

Kevin Rapport · Answer

Have you considered self storage? Remote operations are much easier , especially at scale

James Wachob · Answer

Hey @Thomas Corrar! You’re in a strong position with $100K to deploy, and you’re asking the right questions before jumping in.

Hartford can work, but like a lot of Northeast markets, you’ll often see tighter cash flow due to higher purchase prices, taxes, and older housing stock. That doesn’t make it bad, just more management-intensive and deal-specific. Many investors in your position end up expanding their search into the Midwest or Southeast where the numbers tend to be more forgiving and scalable.

For out-of-state investing, it really comes down to building the right team. I’d start by talking to property managers first, not agents. They’ll give you honest insight on rents, tenant demand, and which areas to avoid. From there, connect with an investor-friendly agent who understands cash flow, not just retail deals. Contractors usually come through your agent or PM once you’re under contract.

With your budget, you’ve got flexibility. You could go duplex for stronger income or a clean single-family for simplicity. Just make sure whatever you buy cash flows conservatively after all expenses, including management.

I work with a lot of out-of-state investors, and one reason markets like Memphis come up often is because your $100K can go much further. Allowing for better cash flow and multiple deals over time instead of just one tighter deal in the Northeast.

You’re on a good timeline aiming for fall. Focus the next couple months on dialing in your buy box, building your team, and analyzing deals consistently. That’s usually what gets people from “research” to actually closing.

Happy to connect if ever the Memphis market peaks your interest!

Eric Fernwood · Answer

Hello @Thomas Corrar,

If your goal is long term financial independence, the chance that you already live in the right city is low.

“Live where you like, invest where you can reach your financial goal.”

Here is the basic process:

• Define the rental income characteristics needed to reach your financial goal.
• Identify a city that can support your income goal.
• Work with an experienced local investment team.
• Identify a tenant segment with the behaviors you need.
• Buy properties that segment already rents.

If you want more details, feel free to reach out.

Income Requirements

Two conditions must be met.

• Rents must grow faster than inflation. If rental income does not outpace inflation, your costs will rise faster than your income.
• Rents must last for the rest of your life. Most companies only last 10 to 18 years, so tenants will need to change jobs over time. Cities must continue attracting new companies so wages remain stable.

City Requirements

Rents rise only when demand increases. Demand increases when people move to a city for jobs.

The city must attract new companies and support business growth so jobs keep increasing. Companies often choose cities with lower operating costs, pro business regulations, lower taxes, and lower crime. They also prefer large metro areas with populations over one million because they provide the labor and infrastructure companies need.

Experienced Local Investment Team

Most information from books, podcasts, and websites is general. But you will buy a specific property in a specific city.

An experienced local investment team understands local conditions, property managers, and reliable contractors. They provide the knowledge, resources, and processes needed to make good decisions.

Tenant Segment Selection

No property ever paid rent; the tenant pays the rent. Your success depends on your property attracting tenants who stay many years, pay on time, and take care of the property. You can identify these tenants by interviewing multiple property managers. Ask a question like this:

“If your goal was to buy properties where tenants stay many years, pay rent on time, and take care of the property, what and where would you buy?”

Property Selection

Once you identify a tenant segment with many reliable renters, determine what and where they currently rent, then buy similar properties.

Bottom Line

This process requires no luck, secrets, or shortcuts. I reverse-engineered it from how successful national retail store chains choose cities, store locations, and inventory to attract their target demographics. It has produced strong tenant and portfolio performance throughout market cycles.

Alfath Ahmed · Answer

OOS investing is easy if you have the right team @Thomas Corrar. First, I would work to identify a good market. I recommend looking in the Midwest since the states are landlord friendly, ton of tech investments, and your money goes so much further.

Connect with a good investor agent that can send you both offmarket/onmarket deals and connect you with their team of lenders, contractors, property managers. Buy deals at 75% ARV rules in B- or C+ areas.

Have your agent help you scope work and use inspection report to create final quote. Make sure you have enough data points from your ARV and use comps as examples to choose layout/materials.

Your $100k should go fair since hard-money is fast and easy. Re-finance the deals and you are all good. Goodluck!

Samuel Eddinger · Answer

Hey @Thomas Corrar.  Welcome to BiggerPockets.  The other posters had some good recommendations.  Hartford is still mostly a D class area but surrounding towns are really good (but likely will not cash flow as well).  It also has rediculously high taxes because the major employer in Hartford is the state itself and the state was carved out from paying any property tax for Hartford.

Specifically, I am a local investor, flipper, and own a property management company in the central CT region.  I'd be happy to have a conversation with you.  If interested, DM me.

Garret Rumbea · Answer

Hey@Thomas Corrar good to meet you. I’m originally from NY but live in CA now. My partners and I invest in larger multifamily out of state. I actually know an operator out in CT who’s looking at deals locally as well. I hear you though. The first deal can definitely feel daunting, especially when you’re investing out of state. I didn’t do it on my own though. Happy to connect if it would be helpful.

Rookie looking where to begin ?

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