Raymond Dickey

AssociationHelpNow

AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments. Hosted by AssociationHelpNow® | Practical insights for managers and boards...

Autor

Raymond Dickey

Kategorie

Education

Podcast-Website

www.buzzsprout.com

Neueste Folge

29. Jun 2026

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Legal, Insurance, Finance & Construction Risks Facing Associations 29.06.2026

HOA & condo boards are being hit from every direction right now: changing laws, rising insurance scrutiny, reserve pressure, construction problems, financing concerns, deferred maintenance, owner disputes, and new questions about how federal housing enforcement may affect emotional support animal accommodation claims. YouTube: https://youtu.be/GP3Kj_ynKMo On-Demand, One Hour, One CEU — Availab...

High-Rise Components That Cannot Be Ignored 31.05.2026

High-rise communities face a different level of risk, cost, complexity, and resident disruption when major building systems begin to age. This one-hour CEU webinar explores why reserve studies are only the starting point, how boards and managers should think about capital planning, and why elevators, facades, balconies, roofs, plumbing, parking structures, fire/life safety systems, maintenance his...

When the Board Turns on the Manager - How to Survive 29.05.2026

When the Board Turns on the Manager - How to Survive It’s more common than most admit—new board members come in and immediately want a change. Instead of a clean transition, some managers find themselves dealing with one or two board members who make their job difficult, unproductive, or even hostile. ———————————————- YouTube: https://youtu.be/bh54uxemLnk ———————————————- In this candid session, w...

Facial Recognition in HOAs and Condos: Access Control, Privacy, Insurance & Legal Risks 27.05.2026

Facial recognition is no longer a future issue for condos, HOAs, high-rises, and community associations — it is already here. YouTube: https://youtu.be/g-KmC6A2gTc CEU video will be available on Jun 30, 2026 12:00 AM EDT at: https://attendee.gotowebinar.com/register/1688654602841957467  In this discussion, our panel looks at how facial recognition and AI-powered camera systems are being used for a...

Access Control — Here’s Where HOAs Get It Wrong 20.05.2026

Gated communities. Key fobs. Call boxes. On paper, it all sounds secure—but many associations are far more exposed than they realize. YouTube: https://youtu.be/kGaplSFlrCA CEUS: You must watch on our GoToWebinar system. Go to www. AssociationHelpNow.com. Join us for a practical discussion featuring Tom Landry (SEC Protects), a 25-year federal law enforcement veteran who retired from the United Sta...

Responsibilities HOA Managers Should Not Accept 06.05.2026

A homeowners’ association manager plays a vital role in the day-to-day operation of a community. However, there are certain responsibilities that should remain with the board and should not be delegated to management. ---------------- YouTube:  https://youtu.be/-pitl_9YrP0 1 Hour CEU Video Available All Day - OnDemand 1h:  Jul 2, 2026 at: https://attendee.gotowebinar.com/register/77977732032656070...

25 Must-Have Policies & Procedures Every HOA Should Have 04.05.2026

Every community association operates on policies and procedures—but many boards don’t realize which ones are essential until a problem occurs. In this livestream, our industry expert panel reviews 25 must-have policies and procedures that associations should strongly consider having in place. ———————————————————————— CEU On-Demand: Available all day on Jun 23, 2026 at: https://attendee.gotowebinar...

One-on-One with Adam Clarkson, Esq. — Real Talk on HOA Legal Risk & Decision-Making 03.05.2026

Join us for an exclusive one-on-one conversation with Adam Clarkson, Esq., as we dig into the real-world legal challenges facing community associations today. This is not a panel—this is a focused, direct discussion designed to unpack how attorneys actually think when boards and managers are making tough calls. We’ll explore where legal risk truly begins (and where it’s often misunderstood), how b...

Things That Kill Insurance Deals: The Mistakes Boards Can’t Afford to Make 02.05.2026

Insurance coverage is getting harder, more expensive, and more complicated for community associations — and small mistakes by boards or managers can create major problems. In this session, insurance professionals Greg Gerelli and Dawn Becker-Durnin discuss the issues that can delay, damage, or even kill insurance deals, including incomplete applications, poor documentation, deferred maintenance, c...

Parking Garages & Concrete Nightmares: What Managers Must Catch Early 02.05.2026

Parking garage and concrete problems rarely appear overnight — they usually start as small cracks, leaks, rust, water intrusion, worn sealants, or hidden deterioration that managers and boards may walk past for months or years. In this discussion, Scott Baryiewski of South Shore Construction and Tanner Oldenburger, PE, RS of Reserve Advisors explain the early warning signs managers should recogniz...

HOA Know-It-Alls — The Psychology of How to Handle Them 11.04.2026

HOA Know-It-Alls — The Psychology of How to Handle Them Every community has one… the “know-it-all.” They’ve read one statute, watched a video, or used AI—and now they’re ready to challenge management, the board, and even legal counsel. Sometimes they’re right. Often they’re not. Either way, they can disrupt meetings, create confusion, and undermine confidence in leadership. In this session, we bre...

Psychology of Groupthink in HOA Boards – When Governance Turns Dysfunctional 01.04.2026

What do high-control groups and dysfunctional HOA boards have in common? —————— YouTube: https://youtu.be/cIZ_4cK9VRY —————— More than most people are comfortable admitting. In this provocative but practical session, we explore the psychology behind groupthink, dominant personalities, loyalty pressure, and information control—and how these dynamics quietly impact HOA and condo board decision-makin...

RFPs That Protect 26.03.2026

Every major HOA or condo project starts long before the contract is signed. ======= YouTube: https://youtu.be/PlAaUJTcYAU ======= It starts with the RFP—and when it’s done wrong, everything that follows can fall apart. In this practical, real-world session, we break down how to structure a Request for Proposal that protects your association, creates true “apples-to-apples” bidding, and reduces the...

AI May Already Be Creating Legal Risk for Your Association 25.03.2026

AI is everywhere—but are community association boards and managers using it safely… or setting themselves up for lawsuits? ========================== YouTube Video Full LiveStream: https://youtu.be/3iRk4l4n56s ========================== In this eye-opening session, we break down the real-world risks of using AI in HOA and condo operations—from confidentiality breaches and copyright violations to i...

Reserve Funding Isn’t a Math Problem 22.03.2026

This interview was based on a recent LinkedIn post from Michelle Baldry. YouTube: https://youtu.be/IzXnCaRJ2sw In her post, Michelle Baldry, PE, PRA, RS as Chair of the Foundation for Community Association Research’s Best Practices shared insights from a national reserve funding survey that highlighted a key issue: many communities aren’t underfunded due to lack of awareness, but because of how di...

HOA Collections Explained 20.03.2026

HOA Collections Explained: Liens, Foreclosure, Bankruptcy, Payment Plans, and Board Collection Mistakes Collecting assessments is not optional for HOA and condo boards. It is a fiduciary duty. But when collections are handled inconsistently or without the right legal process, associations can create serious risk, including selective enforcement claims, Fair Debt Collection issues, confidentiality...

Massive Boulder Blast Update + Can Managers Be Friends With Board Members? 17.03.2026

A routine HOA-area blast turned into a nightmare when huge rocks crashed into homes, damaged association property, and triggered major insurance, liability, and communication issues. In this livestream recording, we revisit one of the most shocking HOA incidents discussed this year and break down what happened next. Were the homes repaired? Who ended up paying? What did the insurance process look...

HOA Special Assessments: How to Communicate Them, Avoid Legal Mistakes, and Decide If Borrowing Is Smarter 15.03.2026

Special assessments are one of the toughest challenges HOA and condo boards face. In this practical livestream, our panel explains how boards and managers can communicate a special assessment without creating panic, avoid procedural mistakes that often lead to disputes or litigation, and evaluate when borrowing may be the better option. The discussion covers owner communication, governing document...

AI in HOAs - Powerful Tool or Legal Time Bomb 13.03.2026

Artificial Intelligence is already inside community associations. ---- This video is not eligible for CEUs ---- YouTube Video: https://youtu.be/kRXYzKmLAzc Managers are using it to draft emails. Boards are asking it to interpret bylaws. Vendors are embedding it into software platforms. But here’s the real question:  Are we using AI wisely — or creating new liability without realizing it? In this l...

HOA Bankruptcy Explained: Can a Condo Association Really Go Broke? 24.02.2026

When an HOA or condominium association files bankruptcy, what actually happens? Can the board just declare bankruptcy? Do owners become personally responsible? Can a creditor force an HOA into bankruptcy? And can a bankruptcy judge really wipe out amenities—or even force massive special assessments? YouTube Video: https://youtu.be/q8w39unoeqI CEU Version: https://attendee.gotowebinar.com/register/...

Protecting Managers & Boards from Abusive Residents 22.02.2026

Have you ever had an owner say something like, “Send me another violation and you’ll regret it. I’ll come down there and deal with you myself”… and you’re left wondering: Is that just rude—or is it a threat? YOUTUBE: https://youtu.be/qpV8O5807do In this conversation, I sit down with community association attorneys, an insurance professional, an engineer, and an on-site manager of a 1,100+ home com...

Maintenance Mysteries - The Hidden Failures That Blow HOA Budgets 14.02.2026

Why do some building failures look simple… until you open a wall and find ten new problems? In this livestream, I sit down with an industry leader who specializes in the toughest maintenance and construction diagnostics facing HOAs today — from mysterious deck failures and chronic mold issues to roof leaks, flashing mistakes, siding cracks, skylight problems, paint delamination, incompatible coati...

CEU VERSION: Dock and Dam Liabilities That Blow Budgets 13.02.2026

Docks and dams age quietly, fail suddenly, and can become budget-wrecking fast if boards and managers don’t spot the warning signs early. This livestream breaks down the hidden structural, environmental, regulatory, and ownership liabilities that too often slip past reserve schedules and end up blindsiding associations with massive surprise costs. We’ll cover what should be evaluated, how to antic...

Dock & Dam Liabilities That Blow Budgets 12.02.2026

Docks and dams age quietly, fail suddenly, and can become budget-wrecking fast if boards and managers don’t spot the warning signs early. This livestream breaks down the hidden structural, environmental, regulatory, and ownership liabilities that too often slip past reserve schedules and end up blindsiding associations with massive surprise costs. We’ll cover what should be evaluated, how to antic...

Hazard Zones - Retaining Walls as a Reserve Problem 11.02.2026

Retaining walls rarely get attention until the ground shifts—literally. This session breaks down why these structures are among the most overlooked high-risk components in community associations and how hidden drainage issues, soil movement, and aging construction quietly set the stage for major failures. YouTube: https://youtu.be/gucX_IWBz6s We’ll cover what managers and boards must document, how...

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