Why Every Contract Needs to Be Reviewed with Becker’s James Robert Caves

08.13.2025
Donna DiMaggio BergerJames Robert Caves, III

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“Most people don’t read the fine print until it’s too late.” This warning from Take It To The Board host, Donna DiMaggio-Berger sets the stage for a crucial conversation with guest and Becker shareholder James Robert Caves about common contract mistakes threatening community associations across Florida.

Drawing on decades of experience drafting, negotiating, and untangling problematic contracts, Donna and Rob reveal why the distinction between proposals and contracts matters, and how seemingly innocent “boilerplate” language can become a community’s worst nightmare. The discussion exposes how vendors strategically include provisions that protect their interests while limiting their liability – often capping damages at the contract amount regardless of the severity of potential future harm.

Among the most dangerous contract provisions are those related to termination rights. Rob strongly advises against agreements that automatically renew and can only be terminated for cause, creating what he calls an “endless loop” where associations remain trapped in unsatisfactory and even dangerous relationships.

Their conversation tackles particularly problematic contract types – telecommunications agreements with decade-long terms, elevator maintenance contracts with right of first refusal clauses, and the emerging trend of non-competition provisions appearing in landscaping and pool maintenance agreements. Through real-world examples, including a $2,500 maintenance contract that resulted in $100,000 damage, Donna and Rob demonstrate why contract review priorities should be based on risk assessment rather than contract value.

Providing practical negotiation strategies while identifying must-have provisions you need inserted into your contracts, this episode delivers essential knowledge for board members and managers who want to protect their communities from costly contractual disasters.

Conversation Highlights: 

  • How boards can ensure the proper legal entity is signing a contract—and why that’s critical
  • The difference between apparent authority and actual authority when directors or managers sign agreements
  • Key clauses every vendor or service contract should include
  • Termination clause traps and what to watch for
  • Common red flags that pop up in community association contracts
  • The enforceability of non-compete and non-solicitation clauses in vendor agreements
  • What makes a contract “illusory” and how to avoid them
  • A practical rule of thumb for deciding which contracts require attorney review—beyond just the dollar amount

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About Take It To The Board

Think you know what community association life is all about? Think again. Residents must obey the rules, directors must follow the law, and managers must keep it all running smoothly. Take It To The Board explores the reality of life in a condominium, cooperative or homeowners’ association, what’s really involved in serving on its board, and how to maintain that ever-so-delicate balance of being legally compliant and community spirited. Leading community association attorney Donna DiMaggio Berger acknowledges the balancing act without losing her sense of humor as she talks with a variety of association leaders, experts, and vendors about the challenges and benefits of the community association lifestyle.

If you’ve got a question, Take It To The Board with Donna DiMaggio Berger – We Speak Condo & HOA!

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Areas of Focus: Condo, Co-Op & HOA, Community Association Litigation & Covenant Enforcement