Thanks for this advice! I hadn't thought about keeping specific documentation of the tax year designation. Will Fidelity automatically generate a receipt showing the 2020 contribution, or should I request something special when I make the contribution?

When you make the contribution online, you'll receive a confirmation that should clearly indicate the tax year. Print this or save a PDF of it. Additionally, I'd recommend taking a screenshot of the contribution page where you select "2020" as the tax year. Fidelity will also generate a Form 5498-SA in May that officially documents your HSA contributions by tax year. This form is sent to both you and the IRS. While you don't need to include it with your tax return, definitely keep it with your tax records. If you want to be extra careful, you can also call Fidelity after making the contribution to confirm it was properly coded for 2020, and make a note of the date, time, and representative's name from that call.

Generally for online transactions, midnight in your time zone on the deadline day is acceptable. However, different HSA providers might have different cutoff times for processing transactions, especially if they require manual verification or processing. To be safe, I'd recommend making the contribution at least 2-3 business days before the deadline. I made this mistake last year trying to fund my HSA on April 15th at 9pm, and while my provider (not Fidelity) accepted it, they initially coded it for the wrong tax year and it was a hassle to get fixed.

This is super helpful! Do you have any specific questions we should ask when interviewing a new CPA to determine if they're more of a #2 or #3?

Ask them: "Do you provide mid-year tax planning meetings?" and "Can you describe your process for identifying tax saving opportunities throughout the year, not just at filing time?" A good #3 tax planner will have clear answers about their proactive approach. Also ask: "What tax planning strategies have you implemented with clients in situations similar to mine?" They should be able to give specific examples without hesitation. Finally, inquire about their fee structure for planning services versus compliance work. True tax planners typically have separate engagement options for planning versus just tax preparation.

This matches my experience too. I switched from a solo CPA to a mid-size firm last year and the difference is night and day. They caught several things my previous guy missed including HSA contribution strategies.

These are great questions I hadn't thought to ask! Do CPAs typically provide some kind of service agreement that spells all this out, or is it more informal? I definitely want to make sure we know exactly what we're getting.

Yes, reputable CPAs will provide an engagement letter that outlines exactly what services are included, their fees, and any potential additional charges. This is a formal document that protects both you and them by setting clear expectations. It's completely normal and professional to ask for this in writing before proceeding. The engagement letter should detail everything - filing which forms, for which states, what happens if you need amendments, audit support terms, and for advisory services, how many consultations you get and what specific planning areas they'll address. If they're reluctant to provide this in writing, that's actually a red flag.

This is a really good point. I've seen TurboTax struggle with multi-state income and self-employment situations. One specific issue to check: TurboTax sometimes doesn't properly allocate income between states when you've moved mid-year, which can lead to double taxation. It also sometimes misses home office deductions for self-employed people.

Thank you all for the advice. I'm definitely going to file now after reading everything. I had no idea the failure-to-file penalties were so much worse than failure-to-pay. I'm going to look into both the installment plan and that Offer in Compromise program. One last question - if I get on a payment plan, will they still put liens on my property or anything like that? I'm renting right now but hoping to buy a house in the next couple years.

Generally, if you're on a payment plan and staying current with your payments, the IRS won't file a tax lien. However, this depends partly on how much you owe. For smaller debts (under $25,000) with an installment agreement, they typically don't file liens if you're compliant with the terms. For larger amounts, they might still file a lien as protection, even with a payment plan in place. The good news is that once you've made enough payments to get below a certain threshold, or if you've been in compliance with your plan for a specified period, you can request for them to withdraw the lien. This is something that changed with their Fresh Start program to help taxpayers.

This is so true. I'm in California and the Franchise Tax Board is WAY more aggressive than the IRS. They suspended my driver's license over a $2200 tax bill I didn't pay. The IRS gives you more time and options generally.

Is CCH Axcess something you can learn on your own though? I thought you needed to work at a firm that uses it to get access. Are there any training resources available for people who don't already work somewhere with these specialized tax software packages?

You're right that it's difficult to get hands-on experience with CCH Axcess without working somewhere that uses it. However, CCH does offer some free webinars and training materials on their website that can at least familiarize you with the interface and capabilities. For specialized tax software, your best bet is to look for YouTube tutorials and documentation online. Many vendors have published training materials that you can access. While it's not the same as hands-on experience, being able to speak intelligently about the software and its capabilities can still give you an edge in interviews. Some universities also have partnerships with these vendors to provide student access - worth checking if your school offers this.

This is a really important point. I think there's often a gap between what companies say they want and what they actually use day-to-day. Have you seen any shift toward using more advanced tools in recent years? Or is it still primarily Excel-based?