I'm actually a bit confused why you need Form 8453 at all? I've been e-filing for years and have never had to mail anything afterward. Most tax software handles everything electronically now.

I had a similar situation last year! The 3 business day rule mentioned earlier is correct - you wait for IRS acceptance confirmation, then mail Form 8453 within 3 business days. One thing that might help with your timing concerns: you can actually prepare everything in advance. Get your Form 8453 ready to go (just don't sign it until after e-file acceptance), put all required attachments together, and have the envelope addressed and stamped. That way, as soon as you get the acceptance email, you can quickly sign the form and drop it in the mail. Since you're leaving April 20th, I'd suggest e-filing by April 15th at the latest to give yourself a buffer. Most e-file acceptances come through within 24-48 hours, so you should have time to mail the 8453 before your trip. Also double-check with your tax software exactly which documents you need to include - sometimes it flags Form 8453 when it's not actually required for your specific situation.

I worked with Credit Karma customers during tax season last year. The official policy as of April 2nd, 2024 is that they don't guarantee early deposits, but in practice, most refunds hit 1-2 days before the DDD. If your DDD is April 12th, I'd expect to see it by April 11th at the latest. If it doesn't show up by end of day on the 12th, that's when you should start investigating. Remember that the IRS sometimes batches refunds differently on holidays and weekends, so timing can vary.

Thanks for sharing your Credit Karma Spend experiences everyone! I'm also waiting on a refund with CK Spend (DDD of 4/15) and this thread has been super helpful. Based on what I'm reading here, it sounds like there's a good chance of getting it 1-2 days early, but it's not guaranteed like some other banks advertise. I've been checking the app obsessively too - glad to know I'm not the only one! Going to try to be patient and check Monday/Tuesday morning. Fingers crossed for all of us still waiting!

Another option if you're still stuck is to check with your tax preparer or CPA if you used one during the years around when you purchased the stock. Sometimes they keep copies of old tax returns that might have records of dividend income from that stock, which could help establish when you owned it and potentially give clues about your purchase timing. Also, don't forget to check your old bank statements if you still have access to them online. Many banks keep records going back 7+ years, and you might find the withdrawal or transfer that funded the stock purchase. Even if it doesn't give you the exact cost basis, it could help narrow down the purchase date and amount, which you can then cross-reference with historical prices. The key thing is to document whatever method you use and keep records showing you made a good faith effort. The IRS is generally reasonable about these situations when you can show you tried to find the actual information.

I went through something very similar about two years ago with an old Fidelity account. What ended up working for me was a combination approach that might help you too. First, I contacted Schwab's customer service and specifically asked to speak with someone in their "account reconstruction" department - apparently they have specialists who deal with exactly these kinds of missing cost basis issues from acquisitions. The regular customer service reps couldn't help, but this specialized team had access to more historical TD Ameritrade data than what shows up in your online account. When that didn't get me everything I needed, I used the IRS's own guidance from Publication 551. They actually have a section that covers "Unknown or Indeterminable Cost" and provides a framework for making reasonable estimates. The key is being able to show you made a good faith effort to find the actual information. I ended up creating a simple spreadsheet documenting: 1) All the places I looked for records, 2) The approximate timeframe I remembered buying (even if it was just "sometime in 2011-2012"), 3) Historical price data from that period, and 4) My reasoning for the estimate I used. I attached this as a statement with my tax return. The IRS never questioned it, and my CPA said this approach shows due diligence while being conservative about not understating the tax owed. Much better than using zero and overpaying significantly.

Don't forget about quarterly estimated tax payments! I do similar expert calls and got hit with an underpayment penalty my first year because I wasn't making quarterly payments. Since you don't have taxes withheld from these payments like your regular job, you're supposed to pay as you go.

Great question about quarterly payments! Generally, if you expect to owe $1,000 or more in taxes when you file your return, you should make quarterly estimated payments. With 4-5 calls at $350-500 each, you're probably looking at $1,400-2,500 in additional income, which could easily put you over that threshold when you factor in self-employment tax. The safe harbor rule is helpful here - if you pay at least 100% of last year's total tax liability through withholding and estimated payments (110% if your prior year AGI was over $150k), you won't face penalties even if you owe when you file. I'd recommend calculating roughly 25-30% of your consulting income and setting it aside for taxes. You can always adjust if needed, but it's better to overpay slightly than get hit with underpayment penalties.

One thing that hasn't been mentioned yet is the importance of understanding how the passive activity loss rules interact with material participation. Even if you qualify for material participation on both properties, your ability to deduct losses may still be limited by your adjusted gross income (AGI). If your AGI is under $100,000, you can generally deduct up to $25,000 in rental real estate losses per year (assuming you actively participate, which is a lower standard than material participation). This allowance phases out between $100,000-$150,000 AGI and is completely eliminated above $150,000. However, if you truly qualify as a real estate professional (which requires both material participation AND more than 750 hours annually in real estate activities, with real estate being your primary business), then the passive loss limitations don't apply at all. Given that you're managing two STRs with all the activities you described, you might actually qualify as a real estate professional, which would allow you to deduct all losses against any type of income. This could be much more valuable than just claiming material participation. Definitely worth discussing with your CPA - the real estate professional status can be a game-changer for tax savings.

Great question! You're absolutely on the right track with material participation. Based on your description, you're clearly meeting multiple tests - likely Test #2 (substantially all participation) since you and your wife handle everything yourselves, and definitely Test #3 (100+ hours with no one else participating more). The renovation property is actually a perfect example of material participation. All those hours you're spending coordinating contractors, making design decisions, purchasing materials, and planning the remodel count fully toward your material participation requirements. The IRS doesn't require the property to be generating income for these activities to qualify. Here's what I'd suggest documenting before your CPA meeting: - Create detailed time logs for both properties (even reconstruct past months from calendars/receipts if needed) - Separate your renovation activities into categories like planning, contractor coordination, material purchasing, and direct oversight - Don't forget to include travel time to/from the property One additional consideration: Given the scope of activities you're describing across two properties plus a major renovation, you might want to explore whether you qualify as a "real estate professional" under IRC Section 469(c)(7). This requires 750+ hours annually in real estate activities and real estate being more than 50% of your work time. If you qualify, you can deduct ALL losses against any income type, not just passive income - which could be much more valuable than standard material participation treatment. Your CPA should be impressed with your level of involvement. You're in a strong position!