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For a more visual approach, I found "The Complete Guide to Your Personal Finances Online" by Scott Bilker really helpful. It has flowcharts and decision trees that make the tax code more visual. The book has a whole section on real estate with clear examples showing how different scenarios affect your tax liability.
Does it cover more recent tax law changes like the TCJA and SECURE Act? I've found many tax books become outdated quickly when tax laws change.
It does cover TCJA changes pretty thoroughly, especially how they impact real estate investors with the new QBI deduction and business interest limitations. The SECURE Act coverage is more limited though, mainly focusing on the elimination of the stretch IRA and changes to RMD ages. The publisher does offer annual updates on their website that cover more recent changes, which helps keep the content relevant even as tax laws evolve. I've found this combination of the book plus the online updates works better than waiting for completely new editions.
Have u guys tried any of the tax softwares like TurboTax or H&R Block? They basically walk u thru everything step by step and explain the tax code as u go. Might be cheaper than buying a bunch of books?
I've used both. They're good for filling out forms but terrible for actually understanding the tax code. They just tell you what to do without explaining why or how things work together. Fine if you just want to file, useless if you want to learn and optimize.
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One thing nobody's mentioned is that if your wife's ITIN is only being used on a joint return with your SSN, you might be able to just attach the W-7 renewal form and her ID docs directly to your tax return when you file instead of doing it separately beforehand. That's what we did last year. Just make sure you're using a tax preparer who knows how to handle ITIN renewals (not all of them do). We learned this the hard way after trying three different preparers!
Thanks for this tip! Do you remember approximately how long it took to process both the tax return and ITIN renewal when you did it this way? I'm wondering if it delays the refund significantly.
When we did it this way, the whole process took about 11 weeks total - definitely longer than a regular tax return. Our refund was held until the ITIN was fully processed. If you're counting on getting your refund quickly, you might want to do the ITIN renewal separately before filing. I'd also add that the IRS sent us a letter about 4 weeks after filing to confirm they received the ITIN renewal application, which gave us some peace of mind during the wait.
Natalie Chen
IMPORTANT: Make sure your wife's name on the ITIN application EXACTLY matches her ID documents. My wife's middle name was spelled slightly differently on her passport vs birth certificate and our renewal got rejected. Had to resubmit everything and it delayed the whole process by months. Also if you're mailing original documents, use a trackable shipping method!! We sent her passport and freaked out for weeks not knowing where it was until it finally came back.
You sent the original passport?? Isn't there any way around that? No way I'm sending my husband's original passport through the mail...
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I use Koinly for tracking all my crypto transfers and it automatically tags them as non-taxable events. Been using it for 3 tax seasons now and it generates all the forms I need for filing. Just another option to consider.
How much does Koinly cost? Their website pricing is confusing with all the different tiers.
The price depends on how many transactions you have annually. I'm on the $99 plan which covers up to 1,000 transactions per tax year. They have cheaper options if you have fewer transactions and more expensive if you're a heavy trader. I've found it worth it because it automatically categorizes everything correctly - transfers, trades, income from staking, etc. You can also manually edit any transactions if needed. At tax time, it generates all the forms needed for filing including Schedule D and Form 8949.
Dylan Cooper
Anyone know if hardware wallets like Ledger complicate this? I transfer from Coinbase to my Ledger for security, then sometimes back to an exchange if I want to sell.
Nope, sending to your Ledger is still just a transfer - not taxable. I document these with screenshots showing the transaction, addresses, and confirmation details. Makes tax time way easier.
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Something else to keep in mind - don't just think about the IRS deadline. If you're filing state returns too, each state can potentially have different rules about their e-file cutoff times. Most follow the federal guidelines, but there are exceptions. I learned this the hard way when I had a California return accepted by the IRS but rejected by the state for being "late" even though I submitted everything at the same time.
Paolo Ricci
ā¢Do you happen to know which states have different deadlines? I'm working on returns for clients in multiple states and now I'm worried...
I don't have a comprehensive list, but I know California strictly enforces their own cutoff time. New York and Illinois have occasionally had different timing requirements too, especially during extension periods. The safest approach is to check each state's department of revenue website directly. Most will have a specific notice about e-filing deadlines on their homepage this time of year. If you can't find clear information, finish those multi-state returns at least 24 hours before the federal deadline to be safe.
Amina Toure
Has anyone had issues with the tax software itself crashing due to high volume? Last year I was filing with TurboTax and their servers got super slow around 10pm on deadline day. Took almost an hour just to transmit a return that normally takes minutes.
YES! This happened to me with Drake last year. The system was crawling and I nearly missed the deadline. This year I'm finishing everything by noon on the final day just to avoid the stress.
Avery Saint
One thing nobody mentioned - check your last paystub of the year and compare the YTD 401k contribution total with what's on your W-2 in Box 12 with code D. They should match. If not, your employer might have made an error. My company somehow transposed numbers in my 401k contribution amount one year and it caused a huge headache at tax time. Better to catch it early!
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Taylor Chen
ā¢Is there a deadline for when employers have to fix W-2 errors? My company is notoriously slow with correcting payroll issues and I'm worried if something's wrong with my 401k reporting, they'll take forever to fix it.
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Avery Saint
ā¢Employers are supposed to issue corrected W-2s (W-2c) as soon as they discover errors, but there's no strict deadline specifically for corrections. However, if you find an error, report it to your employer immediately - they should issue a W-2c within a reasonable time. If your company drags their feet, you can actually report the discrepancy directly on your tax return. The IRS has Form 4852 (Substitute for W-2) where you can report what you believe are the correct numbers based on your pay stubs if your employer won't fix their mistake in a timely manner.
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Keith Davidson
For anyone wondering, the 401k contribution limit for 2025 is $24,000 (or $30,000 if you're over 50). Make sure you're not exceeding that across all your jobs if you have multiple employers with 401k plans. Your W-2 Box 12 code D amounts from all jobs get combined for this limit.
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Ezra Bates
ā¢Does the employer match count toward that limit? I'm putting in about $20k myself but with my employer's 6% match it would go over $24k.
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