I actually did ask HR about this last week after reading some of these comments. They said they're "looking into implementing a pretax transportation program" but don't currently have one. Apparently several other employees have been asking about it too. Did your hospital make you fill out any specific forms to set up the pretax deduction?

Yes, we had to fill out a simple form that authorized the pretax deduction. It was basically just stating that you wanted to participate in the program and acknowledging the monthly amount that would be deducted. Our HR department also mentioned that it took them about 3-4 months to implement the program after they decided to do it, so you might want to follow up periodically. The more employees who ask about it, the more likely they are to prioritize setting it up. We actually started a petition that got over 200 signatures which seemed to finally get management's attention.

This is actually great advice. I switched from driving to taking the bus to my hospital job and not only do I save on parking, but I can use the transit time to relax instead of dealing with traffic. My hospital subsidizes our transit passes too.

Thanks for the farm-specific advice! I do have all my receipts for feed, seed, and maintenance organized by month. I've also got my depreciation schedule from the previous year (2017) that shows the ongoing depreciation of my tractor and irrigation system. Do you think I need anything else specifically for the Schedule F part?

Make sure you have mileage records if you used a vehicle for farm purposes, and documentation for any home office space if you claimed that. Also, if you received any agricultural subsidies or payments from government programs, have those documents ready as well. One more thing - if you had any crop insurance proceeds or disaster payments in 2018, those need to be properly reported. The IRS often cross-references those payments, and discrepancies can trigger further review of your amended return.

Not OP but I'd recommend against using regular consumer tax software for this situation. Those substitute return corrections can get complex and most consumer software isn't really designed for them. Either use a professional or if you're doing it yourself, get the forms directly from the IRS website and fill them out carefully.

I hadn't thought about checking that! Is there an easy way to see what filing status they have for me? Would it be visible somewhere on my paystub? I'm going to dig through everything tonight. Thanks for the suggestion - really hope it's something simple like that.

Check the withholding section of your paystub - there's usually a code or abbreviation that indicates your filing status. It might say "S" for single, "M" for married, or something similar depending on your payroll system. Some companies also have an employee portal where you can view your tax withholding settings. If you don't see it clearly on your stub, definitely call payroll and specifically ask them to verify your W-4 filing status in their system. Sometimes these changes happen during software updates or data migrations and nobody notices until the paychecks are affected.

This is really good advice. Per diem payments should actually be tax-free reimbursements for things like meals and lodging when you work away from your main location. They shouldn't be withholding taxes on true per diem payments at all!

Has anyone done a side-by-side comparison? I'm nervous about missing something if I switch away from TurboTax since they have all my historical data.

I actually did run both TurboTax and FreeTaxUSA side by side the first year I switched, and they came up with identical refund amounts. The only real difference was the interface - TurboTax looks fancier but FreeTaxUSA gets the job done. You can always download your tax return PDFs from previous years and have those for reference. You'll need to manually enter some basic info the first time you use a new service, but after that initial setup, it's smooth sailing. The hundreds of dollars I've saved over the past few years has definitely been worth the small hassle of switching.

This is great advice! I'm in Massachusetts and discovered they have special rules for capital gains on collectibles that are different from federal. Almost missed it until my accountant caught it.

What about if you have 1099 income but it's really small? Like I made only about $3k from a side gig last year. Is that worth paying someone for?

For small 1099 income around $3k, you can probably still handle it yourself using tax software. You'll need to file Schedule C to report the income and expenses, but most tax programs walk you through this process well. Make sure you track all legitimate business expenses to offset that income! The key is keeping good records of your business expenses throughout the year. Even simple things like a portion of your cell phone bill, home internet, or mileage can be deductible if used for your side gig. You'll also need to pay self-employment tax on that income (about 15.3%), but you can deduct half of that on your return.

I used to think the same until I hired a CPA after having kids and buying a house. She found almost $2,800 in deductions and credits that TurboTax missed! Paid for herself many times over. Software only finds what you know to tell it about.