Disciplined acquisition of property requires sourcing, analysis, and negotiation. We represent owners and investors through the full transaction lifecycle, with particular depth in the Chesapeake Bay region and the Florida Keys, and in distressed and auction settings.

What is included

• Property sourcing and identification
• Auction representation and bidding strategy
• Due diligence coordination across legal, environmental, and physical
• Underwriting and financial analysis
• Negotiation support
• Closing coordination

For owners who maintain second homes or who hold property at a distance, we provide ground-level coordination across the operational details that property requires. Our network of vendors and field professionals in both the Chesapeake Bay and the Florida Keys allows us to act with the speed and discretion that absentee ownership requires.

What is included

• Lawn and grounds maintenance coordination
• Vendor management and oversight
• Project oversight (renovation, restoration, capital improvement)
• Materials procurement and logistics
• Personal property services for second-home owners
• Vacation prep and seasonal management
• Cross-region coordination for owners with property in both Virginia and Florida

Selling a property — particularly one held within a structured entity or as part of a long-term hold — requires the same discipline as acquisition. We support owners through the disposition process, with particular attention to the tax and structural considerations that determine net proceeds.

What is included

• Disposition strategy and timing analysis
• Coordination with tax counsel for gain-recognition and basis planning
• Year-ten exclusion election and exit support for QOZ investments
• Listing strategy and broker coordination
• Buy-side due diligence response
• Closing coordination and post-sale entity wind-down

Property businesses require modern digital infrastructure. We design and build websites, tenant portals, and marketing materials specifically for the operators we serve.

What is included

• Custom website development for property businesses
• Tenant portals and management platforms
• Branded marketing materials
• Search visibility and analytics setup

Examples of recent work

For real estate owners and operators who need a strategic partner, we deliver consulting engagements grounded in operational reality.

What is included

• Real estate investment strategy
• Portfolio structuring and rebalancing
• Operational improvement reviews
• Manufactured housing community operations
• Pricing, lease, and revenue strategy
• Process design and documentation

For private clients who require organization and orchestration across the financial professionals in their lives — CPAs, attorneys, registered investment advisors, insurance brokers, and bankers — HMS provides a single point of operational coordination. We do not provide investment advice, tax preparation, or legal counsel. Our role is to ensure that the licensed professionals around the client are working from the same playbook, with the same documents, against the same goals.

What is included

• Personal financial organization and document management
• Coordination with CPAs, attorneys, registered investment advisors, insurance brokers, and bankers
• Cash flow tracking and consolidated owner-level reporting
• Estate planning document coordination
• Insurance policy review and coordination (in conjunction with licensed brokers)
• Investment policy frameworks (in conjunction with the client's registered advisor)
• Family financial governance and decision-making frameworks
• Tax document organization and preparation support (in conjunction with the client's CPA)

Second homes and vacation properties present a distinct set of structural and operational questions. We help owners — particularly absentee owners holding properties outside their primary residence state — design ownership structures and management infrastructure that serve both lifestyle and financial objectives.

What is included

• Optimal ownership structure for second-home assets
• Rental-versus-personal-use analysis
• Tax-efficient operating frameworks
• Property management for absentee owners
• Risk management and liability planning
• Multi-state ownership considerations (Virginia and Florida in particular)
• Estate-planning coordination for legacy properties

The architecture of property ownership matters as much as the property itself. We structure multi-entity portfolios for owners and investors who hold more than a single asset, separating risk, isolating liability, and creating a foundation that supports long-term growth.

What is included

• LLC structuring for residential and investment real estate
• Multi-entity portfolio organization
• Operating-entity versus holding-entity strategy
• Intercompany agreements and operating agreements
• Series LLC and parent-subsidiary frameworks where appropriate
• Coordination with your attorneys and CPAs
• Annual compliance counsel and entity hygiene

Comprehensive advisory for investors deploying capital gains into Qualified Opportunity Zones, from initial strategy through the ten-year exclusion hold. We design structures that meet program requirements and operate them through compliant property selection, capital deployment, and substantial improvement.

What is included

• Capital gains assessment and 180-day deferral planning
• Qualified Opportunity Fund (QOF) formation
• Qualified Opportunity Zone Business (QOZB) structuring and operation
• Property identification within designated zones — Chesapeake Bay region and Florida Keys
• Capital deployment and substantial improvement strategy
• Ongoing operational compliance and reporting
• Coordination with your tax counsel and CPA
• Long-term hold strategy through the year-ten exclusion