Something nobody mentioned yet - if you're performing outside your "tax home" area and need to stay overnight, meals and lodging become travel expenses and different rules apply. In that case, you can definitely deduct transportation, hotel, and meals (100% for 2022 tax year).

As someone who's been working as a session musician for over a decade, I can add some perspective on the "regular vs. temporary" venue distinction that's been discussed here. The IRS actually looks at this more nuancefully than just "same venue = regular workplace." What matters is the nature and expected duration of your work arrangement. For example, if you have a 6-month contract to play at a specific restaurant every Friday night, that's still considered temporary work since it has a defined end date of less than a year. However, if you've been playing at the same jazz club every Tuesday for 3 years with no end date in sight, that would likely be considered a regular work location, making transportation there non-deductible commuting. The gray area comes with ongoing but irregular bookings - like when a venue calls you sporadically for fill-in gigs. In my experience, I treat these as temporary locations since there's no regular schedule or long-term commitment, just individual contracts for specific dates. Also worth noting: if you travel from one temporary work location to another on the same day (say, from a recording session to a performance venue), that transportation between work locations is definitely deductible regardless of whether either location is "regular" for you. Documentation is everything - I keep a simple spreadsheet noting the venue, date, nature of the gig (one-off vs. ongoing contract), and business purpose for each trip.

As someone who prepares taxes, I wanted to add one thing - keep track of any days you work from home! If you're hybrid and don't go to the office every day, make sure you're not paying for parking on days you don't use it. Some parking garages

Another option to consider is carpooling or ride-sharing with coworkers if any live near you! I was in a similar situation and found two colleagues who were also struggling with downtown parking costs. We rotate driving duties and split parking expenses three ways, which brings my monthly cost down from $240 to around $80. Plus we can use the HOV lanes during rush hour which saves time too. It took some coordination at first but now it's routine and we've all become good friends. Might be worth posting on your company's internal message board or asking around to see if anyone else is interested in sharing the cost burden.

Thanks for starting this thread! I'm in a similar situation - my wife and I are expecting our first baby in March and we're also planning to use a birth center with midwives. Reading through all these responses has been super helpful, especially learning about the HSA option and the documentation requirements. One thing I'm curious about - has anyone dealt with expenses for prenatal massage therapy that was recommended by their midwife? Our birth center suggested regular prenatal massage for my wife's back issues during pregnancy, and I'm wondering if that would also qualify as a deductible medical expense since it was medically recommended rather than just for relaxation. Also really appreciate the tips about keeping detailed documentation. Sounds like having everything in writing from the healthcare providers is key, whether you're planning to itemize deductions or use HSA/FSA funds.

This is such great information! I'm actually a tax preparer and wanted to add a few more details that might help you and others in similar situations. For doula fees specifically, the IRS has been pretty consistent that if they're required or prescribed by a qualified healthcare provider (like your midwives), they count as medical expenses. Since your birth center REQUIRED the doula as part of their care protocol, you're in a strong position to claim this deduction. A few additional tips: Make sure to get an itemized receipt from your doula that shows the services provided (prenatal support, labor support, postpartum care, etc.). Also, if your birth center has any written policies about requiring doulas, keep a copy of that documentation with your tax records. Don't forget that travel expenses to and from medical appointments (including doula visits) are also deductible at the standard mileage rate for medical expenses. And if you had to pay for parking at the birth center or any related appointments, those small expenses add up too! The 7.5% AGI threshold can be tough to meet, but with a new baby you might have other qualifying medical expenses like pediatric visits, vaccinations, or any postpartum care that could help you reach that threshold. Good luck with your taxes and congratulations on your new little one!

3 I went through something similar last year buying my uncle's S corp. One thing nobody mentioned to me was the importance of getting a proper business valuation done for the share transfer. The IRS can challenge the valuation if they think the purchase price was artificially low (especially in family transfers). Might be worth getting an independent appraisal documented even after the fact.

Don't forget about the Section 1202 qualified small business stock (QSBS) implications! If your father held the S corp stock for at least 5 years before the sale, and if the business meets certain requirements, you might be eligible for significant tax benefits when you eventually sell. Also, make sure you're documenting the stock basis properly - your basis in the shares will be what you paid for them, plus your share of any S corp income that gets allocated to you going forward (even if you don't take distributions). This becomes really important for calculating gain/loss if you ever sell or if the company is liquidated. One more thing - if you're planning to make any significant changes to the business operations or structure, consider doing it sooner rather than later while you're still in this transition period. Changes made within the first year of ownership are often easier to document and defend from a tax perspective.

This thread has been incredibly helpful! I'm dealing with this same ADP issue right now and was getting frustrated after spending way too much time searching their interface. Based on all the suggestions here, it sounds like the desktop browser + print preview approach is the most reliable method to try first. I appreciate everyone sharing their specific navigation paths too - it's clear that ADP's setup can vary quite a bit between different employers. Going to try the desktop method now and hopefully avoid having to contact HR during their busy tax season. Will report back if I find success with this approach!

I work in HR and deal with ADP implementations regularly - wanted to add a few additional tips that might help! If you're still having trouble after trying all the great suggestions here, check if your company uses ADP's "Essential" vs "Comprehensive" payroll package. The Essential package sometimes has limited employee self-service features, which could explain why certain tax information isn't visible. Also, some companies set fiscal years that don't align with calendar years, so make sure you're looking at the correct tax year (2023 for your current filing). If all else fails, your state's department of revenue website usually has a section about missing employer information - many states will accept your employer's Federal EIN (which should be visible on your W-2) as a temporary substitute while you obtain the state ID. This can prevent filing delays while you sort out the ADP interface issues.