Hands-On Management for Associations --
40 Units or Less

Serving Chicago city and the western suburbs, Pioneer Realty Group combines professional systems, local follow-through, and a named human relationship so smaller associations do not get lost inside a large portfolio.

Small Associations deserve serious management.

Pioneer Realty Group provides hands-on management and administrative support for Chicagoland condominium and homeowners associations, with a particular focus on communities of 40 units or fewer on Chicago's North Side and in selected western suburbs. Smaller associations have many of the same financial, maintenance, insurance, vendor, recordkeeping, and governance responsibilities as much larger properties—but often with volunteer boards doing far too much themselves.

Maybe your treasurer is tracking assessments after work. Maybe one board member knows where every contract and password lives. Maybe repair requests are scattered through text messages and email chains. Maybe the same leak keeps coming back and nobody can easily find the history. Or maybe your board simply spends too much time chasing vendors, scheduling appointments, comparing invoices, and following up on work that should already be finished.

That is the work PRG is designed to take off the board.

We do not believe every association needs the same level of management. Some boards are perfectly capable of governing their community but need someone to operate the software, maintain records, enter data, handle billing workflow, and keep administrative work organized. Other boards need recurring help coordinating vendors, notices, meetings, owner communication, invoices, and open items. And some associations want PRG to manage the routine operation of the property so the board can concentrate on decisions instead of administration. The original service structure was deliberately built around those three levels.

HOA Start Administration is for boards that want to remain highly involved but need the system and records professionally maintained.

Board Operations & Coordination is for active boards that want to make the decisions while PRG keeps the recurring work moving.

Full Association Management is for boards that want PRG handling routine financial, administrative, owner, vendor, and property-management responsibilities while the board continues to govern.

Every PRG association uses HOA Start. Board members change. Volunteers move. Vendors come and go. The association's history should not disappear with them. HOA Start gives the community one organized place for owner records, documents, requests, tickets, communications, board actions, recurring schedules, and other association history appropriate to the service level selected.

Our job is not to create another inbox for the board. It is to create a visible operating system: a named person responsible for follow-through, organized records, clear responsibilities, board-ready information, and open items that stay open until somebody actually finishes them.

And when the issue is bigger than ordinary monthly management—a roof replacement, masonry project, chronic water intrusion, insurance claim, major special assessment, or another substantial capital project—the amount of work changes. Those projects require much more than calling three contractors. They involve scopes, bids, professionals, access, schedules, board approvals, owner communication, change orders, documentation, and persistent follow-up. PRG can provide that additional project oversight under a separately defined scope rather than burying major-project work inside the regular monthly fee. The original plan specifically separated that heavier project work from routine management.

Not sure how much help your association actually needs?

You do not have to know before calling us.

Bring us one board problem.

Schedule a free 30-minute working session and bring the issue currently taking up your board's time—a financial question, vendor problem, maintenance issue, insurance concern, communication breakdown, recordkeeping mess, management transition, or major project.

We will help you sort through the problem, identify what information is missing, determine what belongs with the board versus management or another professional, and talk through the most practical next step. It is meant to be a working conversation, not a generic sales presentation.

[BOOK MY 30-MINUTE BOARD PROBLEM-SOLVING SESSION]

Not ready for a conversation?

[Download the 15-Minute HOA Board Health Check]

Our company specializes in managing multifamily properties and providing top-tier service to our clients. At Pioneer Realty Group, we take pride in our ability to help property owners fill their properties with quality tenants.

We have created a unique database of over 20,000 rental units in Chicago. Our database combines units on the MLS (Multiple Listing Service), our in-house management units, and rental units offered exclusively to select brokerages by some of Chicago's largest landlords. This allows us to provide our clients with the most up-to-date rental comps and help them get top-of-market rent for their properties.

In addition, we are committed to providing stress-free and 100% transparent property management services to our clients. We have a vast network of connections in the maintenance and property management field, which we use to provide our clients with a one-stop-shop for their property management needs. Our services include monthly financial reporting, tenant correspondence, rent collection, surplus disbursement, maintenance calls, 24-hour emergencies, and advice.

Our pricing model is clear and straightforward. Our transparency is second to none, as we provide our clients with the contractor's invoice and our markup to ensure that there are no hidden fees. Additionally, we offer a 30-day mutual cancellation policy to ensure that our clients are satisfied with our services and can make changes if needed.

Given our extensive experience and expertise, we are confident that our services can provide tremendous value to you as a real estate owner. If you have any questions or are interested in learning more about our services, please do not hesitate to reach out. We would be honored to discuss how we can assist you with your property management needs.

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PRG Office Photo

Service Offerings

Which One is Right For You?

HOA Start Administration

Best for Board that primarily need system/data support.

Board Operations & Coordination

Best for Boards that still want to govern and make decisions.

Full Association Management

Best fo Boards that want a management company to handle normal operations.

Team Members


Sean Flynt

Sean Flynt

Founder
Jon Hamilton

Jon Hamilton

Property Manager and Agent
Rachel Simpson

Rachel Simpson

Community Association Manager