Chicago Property Services 2026 Board Member Planning Guide - Annual Board & Maintenance Calendar

Sep 13, 2026

Chicago Property Services 2026 Board Member planning guide supports association directors with a structured year plan for governance, maintenance, and key operational tasks. The guide explains how to complete the operations plan, schedule quarterly board and annual meeting dates, tailor a preventative maintenance plan, and coordinate vendor services. It includes a 12-month calendar framework, administrative and maintenance event tables, and planning sections for capital projects and election activities to improve efficiency and resident community living.

LanguageEnglish

CategoryPresentations

FormatPDF

Pages25

Reading Time9 min

AccessFree to download

Introduction

How to Use this Guide

Community Association Operational Plan

Administrative Events

Preventative Maintenance

Operational Maintenance

Financial/Accounting Events

12-Month Calendar

Planning Checklists & Templates

Board Member’s Planning Guide BUILDING BETTER COMMUNITIES ONE ASSOCIATION ATA TIME 2026 TRANSFORMING COMMUNITY LIVING TRANSFORMING COMMUNITY LIVING CONTENTS Introduction 2 Operations Plan 3 Preventative Maintenance Plan 5 12-Month Calendar 6 5 Year Capital Plan 18 Pre-Board Meeting Checklist 19 Board Meeting Agenda Template 20 Community Association Annual Election Checklist 21 Annual Meeting Announcement Template 22 Annual Meeting Agenda Template 23 [www.chicagopropertyservices.com](www.chicagopropertyservices.com) WELCOME Welcome to the Chicago Property Services 2026 Board Member planning guide. Chicago Property Services is pleased to present this guide to you as a valuable resource. We encourage you to utilize this guide so that you can improve the e ciency and e􀀞ectiveness of the board of directors and improve the community living experience for all your homeowners. How to Use this Guide For maximum impact, we recommend the following: 1. Fill out the operations plan including the quarterly board meeting dates and annual meeting date. 2. Add the operations plan events onto the calendar to ensure the events take place on the dates that you have identiﬁed. 3. Take the preventative maintenance plan and customize it for your association. 4. Identify what vendor will perform the quarterly preventative maintenance plan services and schedule the dates with the vendor. 5. Fill out the working capital plan and identify which capital projects you will want to complete in 2026. 6. Start the project services process to ensure the 2026 capital projects are successfully completed. 7. Fill out the IL Community Association Annual Election Information worksheet to aid in the successful completion of the annual election. 8. Utilize the Pre-Board Meeting Check List and Board Meeting Agenda Templates for each board meeting. 9. Utilize the Annual meeting templates to ensure a smooth and successful annual meeting experience. [www.chicagopropertyservices.com](www.chicagopropertyservices.com) Community Association Operational Plan | Activity/Event | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | Note: | | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | ADMINISTRATIVE EVENTS | Q1 Board meeting(s) | | | | | | | | | | | | | Jan-Mar | | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | | Q2 Board meeting(s) | | | | | | | | | | | | | April-June | | Q3 Board meeting(s) | | | | | | | | | | | | | July-Sep | | Q4 Board meeting(s) | | | | | | | | | | | | | Oct-Dec-budget approval | | Owner’s meeting (annual) | | | | | | | | | | | | | Keep date on or around same date | | Town hall meeting | | | | | | | | | | | | | CPS recommends bi-annually | | Social event | | | | | | | | | | | | | Summer BBQ? | | Contract/vendor review | | | | | | | | | | | | | | | Review of governing docs | | | | | | | | | | | | | | | Surveys-Board to Homeowners | | | | | | | | | | | | | | | Annual census | | | | | | | | | | | | | | | Insurance Renewal | | | | | | | | | | | | | | PREVENTATIVE MAINTENANCE | Spring Service | | | | | | | | | | | | | | | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | | Summer Service | | | | | | | | | | | | | | | Fall Service | | | | | | | | | | | | | | | Winter Service | | | | | | | | | | | | | | [www.chicagopropertyservices.com](www.chicagopropertyservices.com) Community Association Operational Plan | Activity/Event | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | Note: | | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | OPERATIONAL MAINTENANCE | Annual dryer vent cleaning |

FAQs

What should board members complete first in the 2026 planning guide?

Fill out the operations plan, including quarterly board meeting dates and the annual meeting date, then add the operations plan events to the calendar.

How is the preventative maintenance plan used in 2026?

Take the preventative maintenance plan, customize it for the association, and identify which vendor will perform services while scheduling the dates with the vendor.

What types of events are included in the 12-month calendar framework?

The guide organizes administrative events, preventative maintenance services, operational maintenance tasks, and financial/accounting activities across the months of the year.

Sep 13, 2026

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