The Orlando Law Scoop - Small Claims Guide, $450K Raised, and the June 30 HOA Deadline

Rick Brown • May 27, 2025

May Moves with OLG
Q&A Drops, Big Wins, and That June Deadline You

Really Shouldn’t Miss!

As summer starts to sizzle, we’re wrapping up May with major community wins (🍷hello, Wine Quest!), fresh Legal Q&A videos on the way, and one very important certification deadline for HOA and COA boards coming fast.

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Community Corner

29th Annual Wine Quest

This May, we had the honor of sponsoring Quest, Inc.’s 29th Annual Wine Quest — an incredible evening dedicated to raising funds and awareness for individuals with developmental disabilities.


With more than $450,000 raised, the event was a true celebration of inclusion, independence, and the power of community (plus some fantastic wine and good company).


We’re proud to stand with organizations like Quest that help make our community stronger, one meaningful life at a time.


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Need to File a Small Claims Case in Florida? Here’s How.


Sometimes, doing the right thing means standing up for yourself — especially when someone else isn’t holding up their end of a deal.


If you’ve ever:


  • Paid a contractor who ghosted you halfway through the job
  • Been denied a refund for a defective product
  • Lent money that mysteriously vanished with no repayment



You might have a valid small claims case, and you don’t need to hire an attorney to pursue it.


If the amount you’re owed is under $8,000, Florida law gives you the option to file a case yourself in small claims court. And while you can absolutely go it alone, our newest blog and downloadable one-sheeter walk you through what to expect.


You’ll learn:


  • What types of cases qualify
  • How to write a basic demand letter
  • Where to file your claim (hint: it’s not just anywhere)
  • What happens at mediation or trial
  • How to actually collect if you win


💡 Whether it’s $500 or $7,999, you deserve a fair shot at getting your money back. This guide gives you the roadmap, and if you get stuck, we’re always here to help.


📄 Grab the one-sheeter or read the full post Here


Download the Handout

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HOA/COA BOARD MEMBERS!

TIMES ALMOST UP!

Don’t Get Fined. Get Certified.


tarting July 1, 2024, all new HOA and Condominium board directors must complete an approved education course. Existing board members—your deadline is June 30, 2025. No matter the size of your community, this training is essential, and we’re here to help!


🗓 Choose the best time for you from our upcoming course dates.

REGISTER NOW

Legal Q&A: More Videos Coming Soon


Our Legal Q&A video series is just getting started — and your questions are the star of the show.


We’ve already covered everything from HOA headaches to business basics, and we’ve got more answers on the way.


📬 Got something on your mind?

Send us your question — it might be featured in an upcoming video!

Submit Your Question Here!

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Don’t Miss These Must-Read Blogs!

As Florida’s 2025 Legislative Session progresses, several bills could impact how Homeowners and Condominium Associations operate. Notable changes include potential updates to reserve requirements, virtual meeting policies, and investment rules, with the major focus on CS/SB 1742, a comprehensive bill that addresses licensing, public document requirements, and new processes for managing association funds.

Read More

The Ins and

Outs of Contracting

Contracts are a fundamental part of business and personal transactions, from online purchases to business agreements. For a contract to be valid, there must be mutual agreement on terms and an exchange of value. Key elements of a contract include clearly identifying the parties involved, specifying the agreement’s terms, setting dates, and ensuring both parties sign. It’s important to negotiate the terms, clarify responsibilities, and consult a lawyer to ensure the contract protects your interests and meets legal requirements.

Read More

More to Come—Stay Tuned!


There’s always something happening at OLG, and we can’t wait to share more with you soon! If you have any questions, need legal support, or want to join one of our upcoming events, don’t hesitate to reach out. See you next time!

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Start the New Year with Confidence: Your Essential Legal and Financial Checklist for the New Year As we step into the new year, it’s the perfect time to reassess our goals and ensure our affairs are in order. Whether you’re looking to protect your family’s future, streamline your business, or simply get a fresh start, our New Year Reset Checklist is here to guide you. From updating your estate plan to revisiting your insurance coverage, these straightforward tips will help you begin the year with clarity and confidence. Let’s make 2025 your best year yet! N ew Year Reset Checklist Review or Update Your Estate Plan Confirm wills, trusts, and healthcare directives are up to date. Make sure beneficiaries and key contacts still reflect your current wishes. Verify Insurance Coverage Check life, home, auto, or business policies for accuracy and adequate coverage. Add new, high-value items (like holiday gifts) to your policy. Organize Important Documents Safely store originals (wills, titles, deeds) in a secure location. Keep digital backups in an encrypted folder or password manager. Assess Your Finances Review your budget and set savings goals for the year. Check beneficiary designations on bank, retirement, and investment accounts. Consider Charitable or Non-Profit Involvement Think about attending our Non-Profit Bootcamp if you’re interested in establishing or growing a charitable organization. Explore tax benefits and community impact of giving back. Plan for Business Updates (if applicable) Ensure business licenses, permits, and corporate documents are current. Schedule time to review or revise your operating agreements. Schedule Professional Consultations Estate Planning Attorney: Secure or update your plan. Financial Advisor: Review investment strategies, retirement, and tax planning. CPA or Tax Professional: Get organized ahead of tax deadlines. Starting the year off with a clear plan sets you on the right path—less stress, fewer surprises, and more peace of mind. If you need guidance, we’re here to help. Call 407-565-HELP to schedule a consultation or learn more about our services. Make 2025 the Year You Secure Your Legacy Planning for the future doesn’t have to be overwhelming. In our latest YouTube video series, Attorney Erika De Jesus breaks down the basics of estate planning—from wills to trusts. If you’ve been putting off this vital task, now’s the perfect time to learn how to safeguard your loved ones and secure your legacy.
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