Quicken Bookkeeping & Accounting Services
in Chicago
Lewis.cpa sets up and manages Quicken for self-employed professionals, landlords, and small business owners across Chicago and nationwide who want business and household finances tracked in one place. Whether you're starting fresh or cleaning up years of records, our team gets your books organized and keeps them accurate.
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What Makes Quicken Different from Other Bookkeeping Software?
Quicken was built for people running a business and a household at the same time, and that dual purpose sets it apart from software made only for companies.
One File for Business and Personal Finances
Business income and family expenses can live in the same Quicken file while remaining separated by category, making it easier to keep personal and business transactions distinct at tax time.
Built-In Tax Schedules for the Self-Employed
Schedule C and Schedule E reports pull directly from your transaction history instead of a spreadsheet rebuilt from scratch every April.
Rental Property Tracking
Rent rolls, security deposits, lease terms, and per-unit expenses stay organized whether you manage one rental or a small portfolio of properties.
Investment and Net Worth Reporting
Retirement accounts, brokerage holdings, and business equity appear alongside daily cash flow, giving owners a complete financial picture in one place instead of across multiple accounts and logins.
Local File Storage on Your Own Computer
Quicken Classic keeps your data on your own machine instead of a third-party server, an option many owners still prefer for sensitive financial records. A cloud-based version is also available for anyone who wants access from a phone instead.
Our Quicken Bookkeeping and Accounting Solutions
Software alone doesn't keep books accurate. Our Quicken bookkeeping team handles both the initial setup and ongoing monthly maintenance, so your books stay organized without adding another task to your workload.
- Financial Statement Preparation
Profit and loss statements, balance sheets, and cash flow reports pulled straight from your Quicken file, explained in plain terms.
- Quicken Setup and Configuration
Chart of accounts, bank feeds, and category mapping built so transactions land in the right place from day one.
- Splitting Business Activity from Household Spending
A mixed file untangled into properly separated business and personal records, ready for accurate tax reporting.
- Property-by-Property Rental Accounting
Rent, deposits, and maintenance costs tracked by unit, so each property's performance is visible at a glance.
- Investment Accounts Tracked Alongside the Business
Brokerage and retirement accounts linked inside your file, so business cash flow and long-term savings are in one place.
- Mileage Tracking
Mileage logging configured and reconciled against current IRS rates, so every business trip gets deducted correctly.
- Invoicing and Payment Setup
Invoicing and payment tools configured so bills go out on time and payments match the right account.
- Cash Flow Reporting
Reports on what's coming in, going out, and left over, split between business and personal so both stay on track.
- Tax Preparation and Planning
Your Quicken data feeds straight into filing season, so nothing gets rebuilt from scratch.
- Third-Party Integrations
Your Quicken file connected to tools like TurboTax, H&R Block, and Zillow Rental Manager, so tax filing and rental data move over without manual re-entry.
- Quicken Software Training
Hands-on training on logging transactions, running reports, and using the features you'll actually rely on.
- Help When Something in Quicken Breaks
Renamed categories, sync errors, and odd reports get sorted by our team instead of a forum search.
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Stop Guessing What Your Numbers Mean
Get a Quicken file that actually tells you where your business and household finances stand.
Contact UsWho Benefits Most from Our Quicken Services?
Quicken tends to fit certain kinds of businesses and households better than others.
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Landlords can organize rent, security deposits, and maintenance costs by property, while agents and investors can track commission income and monitor how each property performs against the others.
Sole proprietors, family-owned shops, and other small operators keep 1099 income, deductible expenses, and personal spending in one file, with Schedule C reports ready when it's time to file.
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Early-stage founders keep personal and business finances separated from the start, before the business grows into something that needs a dedicated bookkeeping system.
Investment portfolios, retirement accounts, and a side business or consulting practice stay visible together, without switching between several logins to see the full picture.
Which Quicken Version Is Right for My Business?
Quicken comes in several versions, and the optimal fit depends on how you use it, not what you're willing to pay. A freelancer logging basic expenses needs far less than a landlord juggling several rental units or an owner sending invoices alongside a household budget. We tailor the setup to the way your business works, giving you the features you need without paying for ones you’ll never use.
- Quicken Classic Starter
Covers basic budgeting and spending. No investments, loans, or business features.
- Quicken Classic Deluxe
Adds investment accounts, debt payoff planning, and savings goals.
- Quicken Classic Premier
Built for active investors, with deeper portfolio analysis and built-in tax reports.
- Quicken Classic Business & Personal
Adds invoicing, Schedule C/E/F tax reports, and per-unit rental tracking for freelancers, contractors, and landlords.
- Quicken Simplifi
A cloud option for household budgeting from a phone or browser instead of a desktop install.
- Quicken Business & Personal (Simplifi-Based)
The cloud version for solo business owners who need invoicing and tax-ready reports, minus rental property tools.
Our Quicken Setup Process
Most Quicken engagements follow the same general path, adjusted for how much history needs to be brought over and how many accounts are involved.
Initial Conversation
A Quicken consultant from our team talks through how you currently track money, what's frustrating about it, and what you need the software to do for the business and the household.
File and Category Design
We design the chart of accounts and category structure to keep business and personal activity properly separated from the start.
Account Connections
We link bank accounts, credit cards, loans, and investment accounts so transactions import automatically instead of requiring manual entry.
Historical Data Import
We transfer prior transactions, open invoices, and property records so your file starts with a complete picture instead of a blank slate.
Training Session
We walk through the day-to-day tasks, entering transactions, running reports, and reconciling accounts, so you're comfortable using the system on your own.
Ongoing Check-Ins
After setup, we review your file monthly or quarterly, catch anything that's drifted out of place, and adjust as your situation changes.
Why Work with Lewis.cpa for Quicken?
Software setup only gets you started. Lewis.cpa's Quicken professional services go well beyond the initial install, covering the bookkeeping, tax work, and support most owners actually need.
Decades of Bookkeeping Experience
Your Financial Records Stay Under Your Control
More Than Software Setup
One Team for Business and Personal Finances
Flexible Support Options
Client Reviews
FAQs
Does Quicken work on Mac as well as Windows?
Quicken Classic installs on both Windows and Mac computers, though a small set of advanced business and reporting features only appear on the Windows version. We review your platform before setup to ensure nothing you need turns out to be missing later.
Can more than one person access the same Quicken file?
Quicken Classic is built around a single installed copy on one computer, so it isn't designed for several people working in the file at once the way cloud accounting platforms are. Quicken Business & Personal, the cloud-based version, lets owners access their finances from a phone or browser, making it easier to check numbers across multiple devices.
Will my accountant be able to use my Quicken file at tax time?
Yes. Quicken exports reports and transaction data in formats our team can bring directly into your tax return, so your Schedule C or E figures don't need to be rebuilt from scratch every filing season.
What happens if my business outgrows Quicken?
Some businesses reach a point where inventory, in-house payroll, or more complex reporting call for something bigger, since Quicken doesn't include native payroll processing. When that happens, we help move your records to QuickBooks, Xero, or NetSuite without losing your financial history in the process.
Is Quicken cheaper than QuickBooks or Xero?
Generally yes, for a single owner with straightforward needs, since Quicken is priced as a personal finance subscription rather than per-user business software. Quicken also bills annually only, with no monthly option, while QuickBooks and Xero both offer monthly plans. Once a business needs multiple logins, payroll integration, or inventory tracking, the comparison changes and another platform may be a better fit.
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Let's Put Your Quicken File to Work
Reach out to the professionals at Susan S. Lewis, LTD at (630) 548 9600 to explore how our firm can optimize your business's financial operations. Partner with us to build confidence in your financial future.