Year-round tax strategy for business owners and investors.
Tired of only seeing your tax professional once a year when it's too late to make a difference? We partner with business owners, active real estate operators, and crypto investors on proactive wealth retention. We also welcome individuals seeking precision preparation or immediate, federally licensed defense for an IRS or state notice.
What sets Hamilton Tax & Accounting apart
We plan ahead of tax season rather than just recording history after the fact — structuring your transactions to manage your tax liability legally and proactively.
Enrolled Agents & CPAs
The firm's team includes federally licensed Enrolled Agents and CPAs. Enrolled Agents are federally licensed tax practitioners with unlimited rights to represent taxpayers before the IRS.
Year-Round Strategic Advisory
True tax planning happens throughout the year, not on April 14th. We stay in contact through quarterly planning, projections, and timing reviews so there are no surprises when you file.
Practitioner-Operated
Our team members are active business owners and investors ourselves. We apply the same planning, depreciation reviews, and retirement strategies we recommend to our clients.
Built for real estate investors & digital asset holders
At Hamilton Tax, real estate and digital assets are core to what we do — not an afterthought. We pair cost segregation with proactive real estate planning and bring tax-aware guidance to cryptocurrency and self-directed retirement plans.
Cost Segregation & Accelerated Depreciation
Cost segregation separates building components so some can be depreciated faster. We review whether a study fits your property and your overall plan, and pair it with real estate tax planning.
Self-Directed Retirement Plans
Tax-aware guidance for self-directed retirement plans and broader retirement planning, including contributions, distributions, and how your holdings fit together.
Cryptocurrency Reporting
We help clients with record-keeping and reporting for digital-asset activity, and refer specific questions to Steven C. Hamilton II, EA and our staff.
How Cost Segregation Works
Reviewed for fit before you proceed
A cost segregation study separates the components of a building so that eligible parts can be depreciated over a shorter recovery period than the standard 27.5-year (residential) or 39-year (commercial) life. That can mean larger depreciation deductions sooner for the qualifying components.
We don't assume a study makes sense for every property. The team reviews whether a cost segregation study fits your situation and how it fits with your overall real estate tax plan before you move forward.
Steven C. Hamilton II
Founder & Lead Tax Strategist • Enrolled Agent (EA)
Founded in 2013
Your direct ally in tax planning and IRS defense
Steven C. Hamilton II is a federally licensed Enrolled Agent with over a decade of hands-on taxation and advisory experience. An active real estate and crypto investor himself, Steven founded Hamilton Tax & Accounting in 2013 to deliver actionable, year-round tax planning and IRS defense rather than one-off yearly filings.
Hamilton Tax is practitioner-led. Whether representing you during a state Department of Revenue inquiry, reviewing a multi-state partnership, or working through a tax resolution, Steven brings technical tax experience alongside real-world business and investment background.
Unlimited IRS Rights
Enrolled Agents may represent taxpayers before the IRS nationwide.
Digital & In-Person
Visit our Grayslake, IL office or work with us remotely through the secure client portal.
A clear path to get started
Whether you need proactive ongoing advisory or help with a notice, here's what to expect.
Initial Consultation
Book on this page or call our front desk. We review your current situation, look at past filings for missed opportunities, and discuss your business or investment goals.
Secure Client Portal & Review
We invite you to the secure client portal to upload prior returns, W-2s, K-1s, or notice copies. No insecure email — documents stay protected in the portal.
Plan & Defense
We put your tax plan in place, file any needed elections, or represent you before the IRS under a Form 2848 power of attorney when you need defense.
Visit our Grayslake office or connect remotely
We're located on Barron Boulevard in Grayslake and serve clients across the Chicago area and beyond, in person and through the secure client portal.
Office Address
Hamilton Tax & Accounting
790 Barron Boulevard
Grayslake, IL 60030
Phone & Fax
Office: (224) 381-2660
Fax: (847) 557-3913
Office Hours
Monday to Friday, 10 AM to 5 PM Central
Secure Client Portal
Existing clients can upload documents, e-sign returns and engagement letters, check return status, pay invoices, and message Steven and the team through the secure client portal:
- Upload W-2s, 1099s, K-1s, and notice scans
- Secure document delivery & e-signature
- Return status, invoices & staff messaging
Tax preparation, planning, and representation
Year-round tax planning, cost segregation, bookkeeping, IRS and state representation, and more — delivered by Enrolled Agents.
Tax Preparation
Individual, business, estate, and trust returns prepared and reviewed by Enrolled Agents.
- Individual (1040)
- Business (1120-S, 1065, 1120)
- Estate & trust (1041)
Tax Planning
Proactive, year-round tax planning so you make decisions before year-end, not after April.
- Quarterly planning
- Projection modeling
- Year-end strategy review
Cost Segregation
Separating building components so some can be depreciated faster, with a review of whether a study fits.
- Faster depreciation of eligible components
- Feasibility review for your property
- Paired with real estate tax planning
Bookkeeping & Financial Statements
Clean monthly books and financial statements that feed directly into your tax planning.
- Monthly bookkeeping
- Financial statements
- Reconciliations
Payroll
Payroll processing and reporting so your team is paid accurately and on time.
- Payroll runs
- Payroll tax filings
- Reporting
Business Consulting & Entity Selection
Guidance on business structure, entity selection, and day-to-day operations and growth.
- Entity selection
- Restructuring advice
- Growth consulting
Buying or Selling a Business
Tax guidance through the acquisition or sale of a business.
- Acquisition planning
- Sale structuring
- Transition support
Self-Directed Retirement Plans & Retirement Planning
Tax-aware guidance for self-directed retirement plans and broader retirement planning.
- Self-directed plan review
- Retirement planning
- Contributions & distributions
Sales Tax
Sales tax registration, filing, and ongoing compliance support.
- Sales tax filing
- Registration
- Compliance review
IRS & State Representation and Tax Resolution
Representing you before the IRS under a Form 2848 power of attorney for notices, audits, and resolution.
- IRS notice & audit representation
- State tax notice help
- Tax resolution & payment plans
Software Setup
Setup and configuration of accounting and tax software for your business.
- Accounting software setup
- Tax software configuration
- Onboarding
Notary
Notary services available for documents you need authenticated.
- On-site notary
- Document authentication