Honest answer: if your situation is straightforward — one income source, no business activity, basic deductions — you probably shouldn’t switch. The software is genuinely good for simple returns.

Where the math changes: you started a business or side hustle in the last couple of years; your income is high enough that a 1% optimization is worth real dollars; you’ve made a mistake you’re worried about (missed HST registration, unreported income, prior-year errors); you’re thinking about a big decision — incorporating, buying property, taking on a partner; or you’ve gotten a CRA letter and you don’t know what it means.

The DIY software optimizes for what you enter. A CPA optimizes for what you should have known to enter.

Yes — the $30,000 threshold is the trigger for mandatory GST/HST registration. The number is cumulative over four consecutive quarters, not a calendar year.

The day you exceed $30K, you become a “small supplier no more” and you have 30 days to register and start charging HST. People miss this all the time, and CRA can reach back and assess uncollected HST you should have charged your clients. Voluntary registration before you hit the threshold is sometimes the right move — it lets you claim input tax credits on business expenses while you’re under the threshold.

We’ll work through the timing on the discovery call.

You get a small benefit: self-employed Canadians have until June 15 to file their T1, instead of April 30.

But — and this is the part people miss — your balance owing is still due April 30. Interest starts accruing May 1. So if you file in June and owe $4,000, you’ve been paying daily compound interest on that balance for six weeks.

The practical rule: file by June 15, but estimate and pay by April 30.

If you spent money to earn business income, it’s probably deductible. The big categories:

• Home office — a reasonable percentage of rent or mortgage interest, utilities, internet, property tax, insurance, maintenance
• Vehicle — fuel, insurance, repairs, parking, lease payments or CCA — at your business-use percentage
• Phone & internet — business-use portion
• Professional fees — accountant, lawyer, bookkeeper, registration fees, professional dues
• Advertising & marketing — social media spend, website costs, business cards, sponsorship
• Supplies — anything consumable in the course of the business
• Subcontractors — anyone you paid to help you deliver the work (T4As required if more than $500 in services)
• Software subscriptions
• Professional development
• Meals and entertainment — 50% deductible, with strict substantiation rules
• Business travel

What you can’t deduct: ordinary clothing, personal expenses, fines and penalties, golf club dues, life insurance premiums (with narrow exceptions), commuting from home to your principal place of business.

Maybe. The standard rule of thumb people throw around is “incorporate when you’re earning more than you need to live on.” That’s not wrong, but it’s incomplete.

The real factors:

• Tax deferral — corporate small business rate in Ontario is roughly 12.2% on the first $500K. If you’re personally in the 53.5% bracket, leaving money in the corporation defers ~41% until you take it out.
• Income splitting — limited since TOSI rules came in (2018), but still possible with a working spouse paid a reasonable salary.
• Creditor protection — assets inside the corporation are partly shielded from personal creditors (with caveats).
• Costs — annual T2 ($1,500+), separate financial statements, separate bank accounts, legal incorporation costs ($1,500–$3,000), and the operational complexity of running payroll if you take salary.

A rough breakeven: if you’re consistently earning $50K–$75K more than you need to live on, and you expect that to continue, incorporation usually pays back within 2–3 years. Below that, the annual costs often outweigh the deferral benefit.

I’ll run the actual analysis on your numbers — no charge — as part of the discovery process.

Yes, and you’re not the only one. Two paths:

1. Voluntary Disclosure Program (VDP) — if you’re behind and CRA hasn’t contacted you, we can apply for relief from penalties and partial relief from interest. Eligibility is strict, but for someone three or four years behind, it’s often the right path.

2. Just file — if CRA has already sent you a demand letter or you’re not eligible for VDP, we file the returns, deal with whatever penalties get assessed, and then evaluate a taxpayer relief request.

The first move is always the discovery call to figure out what’s actually owed and what relief options apply.

CRA requires you to keep business records for six years from the end of the tax year they relate to. For self-employed people, that means:

• All invoices issued to clients (sequentially numbered, dated, with HST shown if registered)
• All receipts for business expenses (paper or digital — digital is fine if it’s legible and dated)
• Bank and credit card statements for any account where business activity occurs
• Vehicle logbook (date, destination, business purpose, kilometres) if you’re claiming vehicle expenses
• Home office records (square footage, lease, utility bills)
• Cell phone bills if you’re claiming business-use portion
• HST records (collected and paid) if registered

Apps like Dext (Receipt Bank) or QuickBooks Online with mobile receipt-capture make this painless. Setting that up properly in year one saves real hours every year after.

Add it to the return. T4A box 048 (fees for services) is the most common one for self-employed people — clients are required to issue them when they pay you more than $500 for services in the year.

The bigger question is whether you’ve been reporting all of your business income consistently. If the T4A income is less than what you actually invoiced, you’re fine. If the T4A shows more than you reported on your T2125 in a prior year, that’s a problem we should look at, because CRA cross-matches.

Year-round. Email, phone, video. Quick questions (“can I deduct this?”) don’t get billed. Real new work — a new venture, an incorporation, an audit response, a major purchase you want analyzed — gets quoted in writing first.

Practice is in Woodbridge (Vaughan), Ontario. Most work happens remotely — secure document portal, video calls, EFILE. I take Ontario residents and select clients in other English-speaking provinces. Quebec residents need a CPA registered with the Ordre des CPA du Québec for the TP-1 — I refer those out.