Choosing Management

How to Compare Chicago Condo & HOA Management Companies

· August 14, 2026 · 7 min read

Compare Chicago condo and HOA management companies by agreeing on weighted criteria before any proposal arrives, having each director score independently, and then comparing scores as a board. Weight the categories that actually drive service quality: the assigned manager and their capacity, scope of services, financial controls and reporting, responsiveness standards, references from comparable associations, licensure, and total annual cost. Cost is one criterion among several, not the tiebreaker by default.

The reason to fix criteria in advance is behavioral. Boards that discuss proposals without a framework tend to anchor on the lowest fee or on whoever presented most smoothly, then reverse-engineer justifications. Independent scoring against agreed weights surfaces genuine disagreement early and produces a decision the board can explain to owners.

Set the Criteria Before Proposals Arrive

Adopt your scoring rubric at a board meeting before the RFP goes out, and record it in the minutes. Here is a workable starting set of weights; adjust them to your community's priorities.

Suggested weighted criteria

  • Assigned manager and capacity (20 percent) - Who specifically is assigned, their experience with your community type, how many associations they carry, and who covers when they are unavailable.
  • Scope of services (20 percent) - What is included in the base fee versus billed separately, stated in the agreement rather than the pitch.
  • Financial controls and reporting (15 percent) - Accounts in the association's name, board signers, segregation of duties, reporting format and frequency, and board access to live data.
  • Responsiveness standards (15 percent) - Committed response times for owners, directors, and emergencies, and how after-hours calls are handled.
  • References (15 percent) - From associations similar in size, type, and complexity, including at least one that has left the firm if available.
  • Licensure and insurance (5 percent) - Verified through IDFPR, plus appropriate liability and fidelity coverage.
  • Total annual cost (10 percent) - Base fee plus realistic ancillary charges, not the monthly headline.

Score each category one to five with a short written note. The notes matter as much as the numbers when the board reconciles differences.

Make the Proposals Comparable

You cannot score proposals that answer different questions. Send every firm the same RFP with the same required response format, and include your unit count, community type, age, amenities, budget size, current delinquency level, and any known upcoming projects. Ask each firm to submit its standard management agreement with the proposal so the board can compare actual terms rather than marketing language.

Require a total annual cost worksheet

Ask every firm to state, in one table, its base fee and every ancillary charge: resale and disclosure documents, transfer fees, additional meeting attendance, special assessment administration, project oversight, collection administration, portal or technology fees, and copying and postage. Then build your own estimate of the annual total based on your association's real activity level. Rankings frequently shift once that table is filled in.

Interview the Manager, Not Just the Firm

Insist that the specific manager who would be assigned attends the interview. A business development representative is not who your board will work with.

Questions worth asking

  • How many associations do you currently manage, and what is their combined unit count?
  • Walk us through how you would handle a burst pipe at 2 a.m. on a Sunday.
  • Show us a sample board packet and monthly financial report from a comparable association.
  • What does your delinquency process look like, step by step?
  • How do you handle a board that disagrees internally about a decision?
  • What is your transition plan for our first ninety days?
  • What would make you decline to work with an association?

The transition question is especially revealing. A firm with a real onboarding process describes records transfer, banking setup, owner communication, and a documented timeline. A firm without one gives you a reassuring sentence.

Check References Properly

Ask for references from associations comparable to yours, and call them yourself rather than delegating. Useful questions: how long they have worked with the firm, whether their assigned manager has changed and how the transition went, how quickly issues get resolved, whether financial reporting has been accurate and timely, what has frustrated them, and whether they would hire the firm again knowing what they know now.

Also verify licensure independently through IDFPR for both the firm and the assigned manager rather than accepting a claim in the proposal.

Board Checklist

  • Adopt weighted scoring criteria at a board meeting before issuing the RFP.
  • Send an identical RFP with your association's real operating details to every firm.
  • Require the standard management agreement with each proposal.
  • Require a total annual cost worksheet listing every ancillary fee.
  • Have each director score independently, with written notes, before discussion.
  • Interview the assigned manager, not only firm leadership.
  • Request sample board packets and financial reports.
  • Call references from comparable associations yourself.
  • Verify firm and manager licensure through IDFPR.
  • Have association counsel review the agreement before the board votes.
  • Record the selection decision and its rationale in the minutes.

Match the Firm to Your Community Type

A high-rise condominium with elevators, a fire pump, and a doorman has almost nothing operationally in common with a forty-unit townhome association where owners maintain their own exteriors. Ask each firm what portion of its portfolio resembles your community. We maintain distinct condominium, HOA, and townhome programs for exactly that reason, with shared financial management and board support underneath.

Educational Information, Not Legal Advice

This article is general educational information for Illinois association boards and is not legal advice. Governance and contracting obligations differ between the Illinois Condominium Property Act and CICAA, and your recorded declaration and bylaws may impose additional requirements. Have association counsel review any management agreement and interpret your governing documents before the board acts.

Put Us in Your Process

If your board is running a management search, we are glad to respond to your RFP on the same terms as everyone else and to be scored against your criteria. Stellar Property Management serves association boards across Chicago and the North Shore. Contact us to schedule a consultation.

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