Has anybody used the Electronic Federal Tax Payment System (EFTPS) for making estimated payments? I just signed up but it says it takes like 5 business days to get the PIN in the mail. Is there a faster way to make these payments if I need to catch up quickly?

Just want to add some reassurance here - I was in almost the exact same situation two years ago. Missed all my quarterly payments due to a miscommunication with my accountant, but had increased withholding midway through the year. The key thing that saved me was that the IRS considers your total tax payments for the year, not just whether you made the quarterly deadlines. Your increased withholding since May is actually working in your favor more than you might realize. I ended up owing a small underpayment penalty (around $200 for the whole year), but it was nowhere near the disaster I thought it would be. The penalty is calculated monthly on the underpaid amount, so even missing several quarters doesn't necessarily mean huge penalties if your withholding caught up later in the year. My advice: Don't make any rushed decisions right now. Have your CPA run the numbers first to see where you actually stand. You might find that between your increased withholding and the safe harbor rules others mentioned, you're in much better shape than you think. Sometimes the stress of thinking you messed up is worse than the actual financial impact!

Has anyone dealt with property taxes paid to foreign governments? Can those be deducted on US taxes? I'm in a similar situation with my parents buying in Ecuador.

This is such a complex situation! Your parents definitely need to be prepared for ongoing US tax obligations. One thing I haven't seen mentioned yet is the potential impact on their state tax situation. Depending on which state they currently live in, they may need to officially establish tax residency elsewhere before moving to avoid continued state tax obligations. Also, since they're planning to split time between countries, they should be very careful about the substantial presence test. Even though they're US citizens (so it doesn't affect their filing requirement), it could impact how certain deductions and credits are calculated. I'd strongly recommend they consult with a tax professional who specializes in expat taxes BEFORE making the purchase. The timing of when they buy, when they move, and how they structure their finances could significantly impact their tax burden. Getting advice upfront could save them thousands in taxes and penalties down the road.

For anyone still looking for options, I used FreeTaxUSA for my partnership return last year and it was only $69 for the federal Form 1065. Way cheaper than TurboTax ($199) or H&R Block ($149) for the same thing. The interface isn't as slick as the expensive options, but it gets the job done and asks all the right questions. Just make sure you have all your income and expense categories organized before you start.

I went through this exact same situation last year with my small consulting partnership! After researching all the options mentioned here, I ended up using TaxAct Business for around $75, which was a good middle ground between the free manual option and the expensive software. One thing I'd add that really helped me - before you choose any software or method, make sure you understand the difference between guaranteed payments and distributive shares. This tripped me up initially and almost caused me to file incorrectly. The IRS has some good examples in Publication 541 that Malik mentioned. Also, don't forget that partnerships have different deadlines than individual returns - Form 1065 is due March 15th (not April 15th like personal taxes), though you can file for an extension. Since you're filing for 2023, you're already past the original deadline, so you might want to look into late filing penalties and whether you qualify for any exceptions. Good luck with your first partnership return! It's definitely more complex than personal taxes, but once you get through it the first time, future years become much easier.

I'm confused about withholding in these multi-state situations. My company withholds for my resident state (Oregon), but I travel to Washington and California for work regularly. Should I be having them withhold for those states too? Or do I just figure it out at tax time?

Great thread! I'm dealing with a similar situation but with a twist - I'm a freelancer with clients in multiple states. I have clients in Texas (no income tax), New York, and California, and I live in Colorado. From what I've learned, freelancers face even more complexity because we don't have employers handling withholdings. Each state has different rules about when freelance income is considered "sourced" to their state - some base it on where the work is performed, others on where the client is located, and some on where the services are delivered. For example, if I do graphic design work from my home office in Colorado for a New York client, some states would consider that Colorado income, while others might try to claim it as New York income if that's where the "benefit" of my work is received. Has anyone dealt with freelance income across state lines? I'm trying to figure out if I need to file non-resident returns in every state where I have clients, or if Colorado covers it all since I physically perform the work here.

Has anyone noticed that some tax software automatically fills in the payer info if you've used them before? I was entering a bunch of 1099-INTs and realized TurboTax remembered some banks from last year but got confused with the ones that changed names. Double check everything!

This is exactly why I always keep physical copies of my 1099 forms! I learned the hard way that relying on digital copies or memory can lead to transcription errors. Pro tip: if you're entering multiple 1099-INTs, do them all at once while you're focused rather than spreading it out over days. I made the mistake of doing a few one evening and finishing the rest a week later - ended up mixing up some of the EINs because I was rushing. The IRS notices for mismatched information are no joke and can delay your refund by months.