Thanks for bringing this up! I do have about $3,000 a year from a small side gig. Should I be accounting for that directly on the W4 or should I be doing those quarterly payments you mentioned?

For $3,000 in side income, you have two options. You can include it on your W4 by adding the estimated tax amount in Step 4(a) as "other income" which will increase your withholding from your main job to cover it. Alternatively, you could make quarterly estimated payments. This is often better if your side income fluctuates a lot. The rule of thumb is if you expect to owe more than $1,000 at tax time, you should make estimated payments to avoid an underpayment penalty. For $3,000 in extra income, you're probably looking at around $500-700 in additional tax depending on your tax bracket.

This is bad advice. Blanket recommendations like "put an extra $50" don't account for specific situations. That could be way too much or too little depending on income level and other factors. The whole point of the new W4 is to be more precise.

That's a great point I hadn't considered! I did confirm with the parents that the names on the Social Security cards match exactly what we're entering on the return, including middle initials and spelling. Birth dates also match perfectly. The only unusual aspect is that these are twins born in December, but they didn't receive their actual SSN cards until February this year. I'm wondering if maybe the SSA records could have some discrepancy even though the physical cards look correct?

Twins born in December with SSNs issued in February definitely points to the "new SSN not in database" issue. But it's always worth double-checking with SSA directly just to rule out any other problems. You can verify the SSNs with the Social Security Administration by going to their office with your clients (with proper authorization forms) or by having your clients request a Social Security Statement. If everything checks out with SSA, then it's almost certainly just the delay in the information transfer between SSA and IRS systems. Given that information and the timing, I'd probably recommend paper filing now rather than waiting for an extension. Even with the current backlog, the paper return should still be processed well before October.

Which processing center handles returns from Florida? My client is in Miami and I'm helping them with a similar issue.

I completely forgot about state taxes! Do I need to make quarterly payments to the state too, or is that a different process from the federal estimated payments?

Yes, many states require quarterly estimated tax payments similar to the federal system, though the due dates and calculation methods might be slightly different. Your state's department of revenue or taxation website should have forms and information specifically for estimated taxes. Some states even have lower thresholds than the federal government for when you're required to make estimated payments, so don't assume the rules are identical.

I've heard good things about FreeTaxUSA too. Much cheaper than TurboTax but still handles self-employment well. Anyone tried it?

This is such an important point! When my friend got married, her husband had back taxes and liens. When they filed jointly, her refund got seized to pay HIS old tax debts. She was furious because she had no idea this could happen.

Exactly! The IRS calls it "joint and several liability" which basically means both spouses are fully responsible for all taxes due, regardless of who earned the income or claimed deductions. There is something called "innocent spouse relief" that can help in extreme cases, but it's difficult to qualify for and a huge hassle to go through. Much easier to just file separately if you have any concerns about your spouse's tax situation.

This is a great point! Another situation where filing separately can help: income-based student loan repayment. If one spouse has federal student loans on an income-driven repayment plan, filing separately can keep their payments lower since only their income counts.

You're absolutely right about the student loan situation! I forgot to mention that was actually another factor for us. My wife is on an income-based repayment plan for her grad school loans, and filing separately kept her monthly payments about $180 lower than they would have been if we filed jointly. The tradeoff is we lost some tax credits, but the yearly savings on loan payments more than made up for it. Definitely a situation where you need to do the math both ways.

Thanks for the insight! Do you think it would help if I reached out to individual board members instead of just the property manager? Or should I bring it up at the next board meeting?

Definitely reach out to board members directly. Property managers sometimes filter what gets to the board, and your board members might not even be aware of your request. I'd send an email to the board president specifically. Bringing it up at a board meeting is also effective. Put your request in writing beforehand asking to be added to the meeting agenda. When other owners hear about it, they'll likely want the same information, which puts pressure on the board to address it properly. Most board members are just owners like you and would want this documentation for their own taxes too.

This is what I did with my townhouse. Our HOA wouldn't provide individual breakdowns, but I found the property tax line in the annual budget and calculated my share based on square footage. I've been deducting it for years with no problems.