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Homeownership 101: A Simple Maintenance Plan to Protect Your Home Year-Round
June is National Homeownership Month, a time to celebrate the pride, responsibility, and long-term investment that comes with owning a home. Originally established to recognize the importance of homeownership in strengthening communities and building financial stability, the month also serves as an opportunity to educate homeowners on the tools, resources, and best practices that help protect their investment. Throughout June, we'll be sharing information and tips designed to

jessica simpkiss
Jun 103 min read


The Boardroom: The Right Way to Use Surveys in Your Community
Gathering Input Without Creating Confusion Surveys can be a valuable tool for boards—but only when used strategically. Too often, surveys are sent out with good intentions but unclear purpose. The result? Confusion, unrealistic expectations, and sometimes more conflict than clarity. Let’s talk about how to use surveys the right way. Start With a Clear Objective Before sending a survey, ask: What decision are we trying to inform? Is community input appropriate for this topic?

jessica simpkiss
Apr 302 min read


Behind the Scenes: The Work Volunteers Do for Your Neighborhood
Serving on a board might sound simple on paper: attend a few meetings, make a few decisions, call it a day. In reality? It’s so much more. What most people don’t see is the behind-the-scenes work that happens between meetings—the emails, the reviews, the problem-solving, and the constant balancing act of doing what’s best for the entire community. Let’s take a closer look at what board members are really doing: 📧 Responding to resident concerns - From simple questions to co

jessica simpkiss
Apr 282 min read


The Boardroom: From Complaints to Contributions
Turning Feedback Into Action Every board hears it—the complaints, the concerns, the strongly worded emails. And while it’s easy to view these interactions as disruptions, there’s often an opportunity hiding inside them. Because behind many complaints is something valuable: engagement. The question is—how do you turn that into something productive? Listen for the Underlying Issue Not every complaint is presented clearly—or calmly. But buried in frustration is often a legitimat

jessica simpkiss
Apr 232 min read


The People Behind the Community: How Volunteers Keep It All Running
When you drive through your neighborhood and everything feels… just right —the landscaping is maintained, the lights are working, the finances are steady, the rules are being upheld—it’s easy to assume it all just happens . But it doesn’t. Behind every well-run community is a group of volunteers working diligently to keep things moving forward: your HOA or condo board. These individuals are responsible for some of the most important decisions affecting your community, includi

jessica simpkiss
Apr 141 min read


The Boardroom: Committees That Work
How to Recruit, Structure, and Retain Volunteers Committees can be one of the most powerful tools a board has—or one of the fastest ways to create confusion. The difference comes down to structure. When done well, committees extend the board’s capacity, bring in valuable expertise, and increase community engagement. When done poorly, they lead to frustration, inefficiency, and blurred lines of authority. Let’s talk about how to get this right. Start With Purpose—Not People On

jessica simpkiss
Apr 72 min read


National Volunteer Month: A Thank You to Our Board Members
April is National Volunteer Month, and in community associations, there’s a group of volunteers who deserve a very specific—and very enthusiastic—thank you: your Board of Directors. These are the people who step up. Who raise their hands. Who says, “I’ll help.” And then quietly take on one of the most complex (and often misunderstood) roles in a community. Board members aren’t paid. They don’t clock out at 5:00. And they certainly don’t sign up because it’s easy. They volunte

jessica simpkiss
Apr 41 min read


Board vs. Management: Who Does What? (And Why It Matters)
If you’ve ever found yourself thinking, “Wait… is this something the board should be doing?” — you are absolutely not alone. This is one of the most common questions we hear from board members. And honestly? It makes sense. Community associations are a unique little world where volunteers, professionals, vendors, attorneys, accountants, and homeowners are all working together at the same time. Without clear roles, things can get confusing fast. So let’s talk about it. Fi

jessica simpkiss
Mar 313 min read


How Boards Can Plan for Spring Projects Without Blowing the Budget
There’s something about spring that makes boards feel ambitious. The sun comes out. The property starts waking up. Owners start emailing. And suddenly everyone has ideas. “Can we redo the entry sign?” “The mulch looks terrible.” “We should pressure wash everything.” “What about new benches?” “Didn’t we say we were going to address the pond this year?” Spring has energy. And energy is wonderful — until it collides with a budget that was adopted three months ago. Here’s the tru

jessica simpkiss
Mar 243 min read


The #1 Mistake New HOA Boards Make: Trying to Rewrite the Rules Too Fast
It happens almost every time. A new board gets elected. There’s fresh energy, new ideas, and a strong desire to make improvements. Maybe the previous board wasn’t communicating well. Maybe enforcement felt inconsistent. Maybe the community has been frustrated for years and finally voted for change. And within the first few meetings, someone says it: “We need to rewrite the rules.” On the surface, this makes total sense. Rules feel like the fastest way to fix problems. If

jessica simpkiss
Mar 173 min read


The Ultimate Spring Checklist for Communities
Because spring in a community association isn’t just about flowers — it’s about function. Spring hits differently in community associations. It’s not just sunshine and pollen (so much pollen). It’s budget season follow-ups, reserve conversations, landscaping contracts kicking into high gear, architectural requests rolling in, and owners suddenly remembering that yes — they do, in fact, live in an HOA. For boards and managers, spring is the unofficial “new year.” It sets the t

jessica simpkiss
Mar 104 min read


The Boardroom - I Just Got Elected to the Board… Now What?
If you’ve recently been elected to your HOA or condo board, there’s a good chance you’re feeling a mix of pride, curiosity… and maybe a little panic. Most board members don’t run because they have experience in governance, finance, contracts, or risk management. They run because they care about their community and want to help. Then suddenly, after the election, reality sets in: Wait… what exactly am I supposed to do now? Here’s the truth many new board members aren’t told: y

jessica simpkiss
Mar 33 min read


Why Communication Is the #1 Issue in Associations — and How to Fix It
Ask almost any board, manager, or homeowner what causes the most tension in community associations, and the answer is usually the same: communication. Not budgets. Not maintenance. Communication. The good news? Communication issues are fixable—when approached intentionally. Why Communication Breaks Down Most communication problems don’t stem from bad intentions. They usually come from: Unclear expectations Delayed responses Inconsistent messaging Emotional reactions during st

jessica simpkiss
Feb 171 min read


Easy Ways Boards Can Improve Community Culture
Community culture doesn’t happen by accident—it’s shaped by everyday decisions, communication, and leadership. While boards can’t control every interaction between neighbors, they can set the tone for how a community feels, functions, and grows together. The good news? Improving community culture doesn’t require a major overhaul. Small, intentional changes can make a meaningful impact. 1. Lead With Transparency Residents feel more connected when they understand what’s happen

jessica simpkiss
Feb 32 min read


Five Things Every Board Should Be Doing in January
January is the calm before the calendar fills up. It’s the one time of year when boards can pause, reset, and get ahead of what’s coming—before projects ramp up, budgets get tight, and meetings start feeling rushed. The communities that stay steady throughout the year usually have one thing in common: they used January wisely. Here are five things every board should be doing at the start of the year to set themselves up for success. 1. Get Organized as a Board January is the

jessica simpkiss
Jan 212 min read


How to Set Your Community Up for Success in 2026
There’s something about January that makes everything feel possible. New calendars. Clean spreadsheets. Fresh agendas. For community associations, it’s also the moment when good intentions either turn into strong systems—or quietly drift until the year starts running the board instead of the other way around. Setting your community up for success in 2026 doesn’t require a massive overhaul. In fact, the most successful associations usually focus on a few simple things done wel

jessica simpkiss
Jan 72 min read


The Human Side of Community Management
Behind every well-run community is a manager balancing countless responsibilities—owners, vendors, Boards, compliance, emergencies, and the day-to-day details that keep communities functioning smoothly. It’s a role that requires professionalism, patience, and consistency, often under pressure and with little visibility into the human side of the work. We wanted to share the following reflection from one of our managers because it offers insight into something boards don’t a

Jennifer Grant
Dec 16, 20253 min read


Looking Ahead to 2026: What Homeowners Can Expect Next Year
As we close out another busy year, our team at myStreet Community Management is already hard at work preparing for a smooth, successful 2026 for all of our communities. Whether you’re a long-time resident or new to the neighborhood, we want you to feel informed, prepared, and confident about what’s ahead. Here’s a look at what homeowners can expect going into the new year: ✨ A Focus on Proactive Maintenance Many communities have important preventative and long-term mainte

jessica simpkiss
Nov 20, 20252 min read


🏡 The Power of Planning: Why Every Community Association Needs an Annual Plan
Running a community association is a lot like running a small business — success doesn’t happen by accident. It takes organization, foresight, and teamwork to keep everything on track. That’s where an annual plan comes in. Think of it as your community’s roadmap for the year ahead — outlining what’s coming, who’s responsible, and when things should happen. A solid annual plan helps your board stay proactive rather than reactive and ensures that every decision connects back to

jessica simpkiss
Nov 6, 20253 min read


Planning for the Future: Helping HOA Boards Think Beyond One Budget Cycle
For most HOA boards, the annual budget is the cornerstone of operations, covering everything from landscaping contracts to reserve...

Athena Tavuchis
Oct 1, 20252 min read
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