Should I buy close or in growing markets?

[Daniel Lenders]

Hi everyone! 

I've been lurking here for a while now, but I am getting close to making the jump into real estate investing. I have a decent down payment in place, but I'm struggling to commit on a singular idea of what I want to do. 

My dad has been in real estate for 40 years now. He's a contractor and always bought close because he could go and fix things when they went wrong, update the property when the renters left, etc. 

I'm wondering about strategy. I'm currently in MA, in a suburb close to Boston. Should I stick close to be able to keep an eye on things? The market here is steep, landlord rights are harder than other states. 

I was also thinking about STR as well, but that is a whole other business.

I'd love a little advice for a new investor in RE to help give some direction! 

Thanks in advance! 

[Melissa Justice]

@Daniel Lenders,

Hey there and welcome to the forum and props to you for taking that next step after doing your research. You’re in a great spot with a down payment ready and a solid mentor in your dad!

It’s totally normal to feel torn between strategies, especially when you're weighing what worked for someone else (like your dad) against what makes sense in today’s market. Given that you’re in Massachusetts, here are a few thoughts:

Staying Local:
Being nearby gives you peace of mind and control, especially with your dad's contractor experience, but MA is expensive, heavily regulated, and not very landlord-friendly. Your ROI may be lower and cash flow tight, especially as a first-time investor.

Out-of-State Investing:
You don’t have to invest close to home. Many investors today are building passive income streams through turnkey rentals in the Midwest and Southeast, where homes are more affordable, landlord laws are favorable, and cash flow is stronger from day one. Think of it as buying based on data, not distance.

STRs:
You’re absolutely right - short-term rentals are a whole different business. If you’re ready to manage guest turnover, dynamic pricing, and regulations, it can be profitable, but if your time is limited, you might consider mid- or long-term rentals for a more manageable start.

My Take:
Since you’re just getting started, I’d recommend keeping it simple:
Go with a long-term or turnkey rental in a cash-flowing market (think Birmingham, Indianapolis, Citrus Springs FL, etc.)
Use that first property to build confidence, systems, and passive income
Then explore more active or complex strategies like STR or BRRRR if/when you're ready

Happy to always help with identifying the right markets or running numbers.

You’re doing it right by taking the time to plan - excited for you to get that first deal under your belt!

Best of luck,

Melissa