tax strategy

Virtual Accounting & Tax Strategy for Real-Estate Investors (US-based)

Deviating from the norm - year round tax strategy and implementation.

Abstract graphic with three dark teal and one lime green curved arrow shapes radiating outward from a central point.
With Anomaly, you get clear, audit-ready financials that match your tax returns—and a documented tax strategy executed monthly, not scrambled together at year-end. We handle portfolio-level bookkeeping by property, capex tracking, debt schedules, and the tax strategy that matters: REPS qualification, STR participation tests, depreciation and cost segregation timing, and 1031 exchange planning. The result is cleaner NOI visibility, losses that flow through correctly to offset your income, and the confidence that your books and tax strategy are working together.
Portfolio-level accounting & tax strategy

What we do for real estate investors

Portfolio-level bookkeeping, capex tracking, debt schedules, and proactive tax strategy - executed monthly, not scrambled at year-end.

Clear Financials

Audit-ready books that match your tax returns exactly.

Monthly Strategy

Documented plan executed monthly, not scrambled at year-end.

Portfolio Tracking

By property: bookkeeping, capex, and debt schedules.

REPS Qualification

The tax strategy that matters for real estate investors.

Award-winning impact: Recognized excellence in client services

Our team has been recognized for our impact
and services to clients. Recent awards include: Greg O'Brien (3x) and John Malone (2x) as 40 Under 40, AccountingToday Top 10 Firms for Tech, the #1 Tax Strategist of the Year Award by the American Institute of Certified Tax Planners & Forbes Magazine Top 200 CPA Firms.

2026 Forbes Best-in-State Top CPA

2025 Forbes Best-in-State Top CPA

2024 Forbes Top 200 CPA Firms

Two CPA Practice Advisor logos: left side shows '40 Under 40' in purple and gray; right side shows '20NTY Under 40 Influencer' in dark red and gray.

2022 CPA Practice Advisor "40 Under 40" professionals who have emerged as leaders in the profession.

Accounting Today 2022 Best Firms for Technology badge.

2022 Accounting Today Best Firms for Technology

2021 Concierge Accounting Firm of the Year

Gold seal emblem with initials CTP and text Certified Tax Planner around the edge.

2020 AICTC Tax Planner of the Year National Finalist

We're problem solvers first. We learn your goals, underwrite the tax angles, and build a practical, documented plan — so you feel confident you're capturing every legitimate opportunity while staying within the lines.

Tailored tax solutions for real estate investors

Don’t settle for a tax planning process that just skims the surface. Think differently.

At Anomaly, we empower our clients to take control of your tax journey by providing a comprehensive review and planning process from the get-go. But we don’t stop there. Our team is dedicated to delivering high-impact and proactive tax strategies tailored to your unique situation.

Identify

Identify actionable tax strategies that apply to your unique situation

Implement

Seamlessly implement the tax strategy to your current system on the fly

Report

Properly report the strategy on your tax returns

Accounting Services

Accounting Services for Real Estate Investors

Real estate timelines, capital stacks, leases, and debt terms create a different equation for every company. Whether you develop, manage, invest, broker, or represent properties, our team brings investor-grade accounting and practical, on-the-ground insight.

You can expect investor-grade accounting combined with practical, on-the-ground insight — tailored to your portfolio and growth goals.

our clients say

Anomaly CPA's client
victories in the spotlight

Innovative business owners and investors across the globe benefit from our unique tax strategy and cloud accounting experience allowing them to stay ahead of the curve.

CLIENT SPOTLIGHT

"Anomaly helped me out with starting my own business. I could tell right away that they were extremely knowledgeable and passionate about helping their clients navigate the complex world of taxes and creating effective strategies to reach their goals."

Mark Perlberg
CLIENT SPOTLIGHT

"I would recommend Anomaly to anyone. They have been an extremely valuable asset to our business and acts as an extension of our team. We began working with Anomaly almost 2 years ago and it was a great decision. They are extremely responsive and I would highly recommend their services to anyone."

Dan Bresciani
CLIENT SPOTLIGHT

"Anomaly provides a professional and tailored approach to achieve the desired outcome for clients and we couldn’t be happier with the quality of his services. They've helped us manage through the first year of our new company and taken the stress out of dealing with multiple vendors, agencies and tax authorities making year one seamless for our business. We look forward to another successful year and would highly recommend their services!"

Jay Carlington
CLIENT SPOTLIGHT

"Anomaly, has been INSTRUMENTAL to the success of our start-up business. Their knowledge, expertise, and due diligence in the accounting field gives us the confidence that our books will always be in good hands as we continue to focus on other pertinent business matters. I would recommend Anomaly to anyone looking for a fantastic service on a budget! Thank you for being awesome!"

Brian Megill | Host Events Inc.
CLIENT SPOTLIGHT

The biggest difference that we noticed right away was that there were all these things that we could be taking advantage of.

We could be way more strategic with how we were filing, what strategies we had in place, and what things had been ruled on from a tax law perspective.

My favorite part about it is, at the highest level— because there are tiers that you can work with the team through— but at the highest level, you’re fully supported.

Your accounting is taken care of. All of your tax strategy is taken care of. Basically anything you would need on the back end, money-wise, you’re taken care of.

That even includes if an audit were to come up or something like that. You have support with all of that. Love it. So grateful.

Nexus Family Chiropractic
CLIENT SPOTLIGHT

I would wholeheartedly recommend Greg O’Brien and his entire team to any small business or mid-sized business owner looking for help.

We don’t have the resources, and often don’t have the budgets, to bring on staff full-time.

Honestly, Greg and his team have been the next best thing.

John Guilfoil Public Relations
CLIENT SPOTLIGHT

I’ve been a client since day one,
and I’m just so proud of him,
seeing him build this up.

Now he’s helping so many people—
so many entrepreneurs,
so many businesses,
so many investors,
so many individuals and companies. It’s been incredible.

I’ve been working with him and his team
for, yeah, must be four years now. And I would say, if you’re an entrepreneur,
you own businesses,
or you’re a high earner
and you have investments like real estate,
working with Greg is an absolute no-brainer.

They’re forward-thinking.
They’re cutting-edge.
They’re leaders in the space.

I know personally, for me,
they’ve saved me a lot of money,
which has been able to add to my net worth.

I’ve saved way more than they’ve cost,
or the investment in them.And it’s so worth it.
So much so.I’ve recommended dozens of people to them.

Wade Critides | Lifestyle Entrepreneur
CLIENT SPOTLIGHT

I discovered them through some research on Google, actually.
I had just moved to Massachusetts, and I needed a Massachusetts accountant, somebody to come and partner with me.

I’ve been using them for about two years now.
They are great partners.

They really support me in my business, and I highly recommend them.

I feel they can support any industry with all their accounting and tax needs.

C.Kay International

Real Estate FAQs

Frequently Asked Questions About Accounting & Tax Strategy for Real-Estate Investors

Can you handle REPS/STR planning?

Yes we specialize in REPS and STR tax strategy. We offer a full course on the STR tax strategy and have been cited by Biggerpockets (https://www.youtube.com/watch?v=xOcPEqb4t6Y) for our STR tax strategy work.

What unique approach does Anomaly CPA take toward tax strategy and planning?

Anomaly CPA goes beyond traditional tax planning by integrating year-round strategic planning and implementation, ensuring businesses maximize every tax opportunity with customized strategies. This approach led to Anomaly CPA being named the #1 Tax Strategist in the US in 2023 by the AICTC.

Discover a partnership for transformational growth.

With base level tax advisory subscriptions starting at $450/month + bookkeeping starting at $500/month, our engagements are relationship based, combining initial strategy, implementation and ongoing support. We work with our clients throughout the year to help them transform their business. Please answer the questions on the following page so we can determine if we are a mutual fit.

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