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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
45 minutes ago3 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


Being Board-Ready: How to Approve Your Association Budget with Confidence
When a board meets to adopt its annual budget, it’s not just a line-item process—it’s one of the most important governance decisions...

jessica simpkiss
Sep 12, 20252 min read


The Value of Attending HOA Meetings (Even Just Occasionally)
Homeowners’ Association (HOA) meetings aren’t always at the top of everyone’s to-do list, but attending, even occasionally, can offer...

Athena Tavuchis
Jul 31, 20252 min read


Understanding Your Association’s Budget: What It Is, Why It Matters, and How It Affects You.
If you live in a homeowner's or condominium association, you’ve likely received a copy of the annual budget, or at least noticed your...
Jessica Simpkiss
Jul 17, 20253 min read


Safe, Fun & Inclusive: Summer Tips from Your Association Management Team
Summer is here, and across the many communities we manage, residents are ready to relax, recharge, and reconnect with neighbors. Whether...
Candice Wojnarowski
Jun 16, 20252 min read


Spring has Sprung!
Springtime Preparations for Your Community: Ponds, Landscaping, and Pool Season on the Horizon As winter fades and spring approaches,...
Jessica Simpkiss
Mar 24, 20253 min read


Understanding the Corporate Transparency Act: What Your Association Needs to Know Before the March 21, 2025 Deadline
The Corporate Transparency Act (CTA) has been a hot topic for businesses and organizations nationwide, and community associations are no...
Jessica Simpkiss
Mar 24, 20252 min read


Prepare Your Community for Impending Bad Weather
When winter storms approach, community associations must act swiftly and strategically to ensure safety and minimize disruption....
Jessica Simpkiss
Mar 24, 20253 min read


Reflecting and Appreciating: A Year in Review for Our Community
As the year winds down, it’s a wonderful time to look back on everything we’ve accomplished together. December isn’t just for holiday...
Jessica Simpkiss
Mar 24, 20252 min read


The Importance of Planning: Why Your Community Association’s Annual Plan Matters
As the new year approaches, there’s a lot of excitement in the air. And while some people are thinking about resolutions, community...
Jessica Simpkiss
Mar 24, 20252 min read
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