One thing nobody mentioned is that if you claim your baby, you might qualify for Head of Household filing status which has better tax rates than filing Single. You need to provide more than half the cost of keeping up the home where your child lives. In my situation, I was the lower earner but by claiming our baby and filing HOH, I saved way more than my higher-earning partner would have saved by claiming her. Just another factor to consider when you're figuring this out - don't just look at the child tax credit alone!

This is such a common situation for unmarried couples! I went through something similar last year. A few key things to consider beyond what others mentioned: Since your boyfriend is self-employed, he can also potentially benefit from the Additional Child Tax Credit if his tax liability gets reduced to zero - this credit is refundable unlike the regular Child Tax Credit. With his business expenses and the child-related credits, he might end up with a nice refund. Also, don't overlook childcare expenses if either of you paid for daycare or a babysitter so you could work. The Child and Dependent Care Credit can be worth up to $1,050 for one child, and whoever claims the child gets this benefit too. One strategy some couples use: run a quick calculation using tax software both ways before filing. Most programs let you play with different scenarios. Enter all your info twice - once with you claiming her, once with him claiming her - and see which gives your household the better overall result. And definitely look into that Head of Household status! The tax savings from HOH filing status alone might outweigh the benefit of your boyfriend claiming the higher credits, especially since you're already paying most of the housing costs.

Something nobody has mentioned yet - make sure you have a clear business plan and documentation showing your intent to make a profit! If you claim business losses for too many years, the IRS might reclassify your business as a hobby, which would disallow your deductions. This isn't an issue in your first year at all, but keep good records showing efforts to generate revenue, marketing attempts, business development, etc. The IRS generally looks for profitability in 3 out of 5 years for most businesses (5 out of 7 for horse-related businesses, oddly enough).

I'm dealing with a similar situation with my new consulting LLC! Reading through all these responses has been incredibly helpful. One thing I want to add from my recent experience - when you do file your Schedule C with losses, make sure you keep EXCELLENT records of everything. I just went through this process and learned that the IRS is particularly interested in seeing that new businesses are legitimate profit-seeking ventures, not hobbies. Beyond just keeping receipts, document things like: - Your business plan and revenue projections - Marketing efforts (even if unsuccessful initially) - Time logs showing hours worked on the business - Any client outreach or networking activities Even though you're totally allowed to claim losses in year one (despite what that H&R Block preparer told you!), having this documentation ready shows the IRS you're running a real business. It also helps if you ever get questioned about the hobby loss rules that others mentioned. The equipment expenses you mentioned should definitely be deductible - either through Section 179 immediate expensing or regular depreciation. Don't let anyone tell you otherwise!

Just to add something nobody's mentioned - check with your tax professional about any potential STATE tax benefits for your vehicle purchase. While federal deductions for personal vehicles are limited, some states offer credits or deductions for certain vehicle purchases that are more fuel-efficient than previous models.

Hey Kyle! I went through the same confusion when I bought my car last year. The key thing to remember is that for a regular personal vehicle used mainly for commuting, there aren't any federal tax deductions available. The IRS considers commuting a personal expense, not a business one. However, don't give up hope entirely! Here are a few things to check: 1. **Electric Vehicle Credit**: If your $38,500 car happened to be electric or a qualifying plug-in hybrid, you might be eligible for up to $7,500 in federal tax credits. Check if the manufacturer and model are on the IRS qualified vehicle list. 2. **Business Use**: Even if it's your personal car, if you use it for any work-related travel beyond your normal commute (like driving to different job sites, client meetings, or business errands), you can deduct those miles. You'd need to keep a detailed mileage log though. 3. **State Benefits**: Many states have their own vehicle incentives that are separate from federal rules. Since you're in Pennsylvania, definitely look into any state-specific credits for newer, more efficient vehicles. The documents you'd want to keep are your purchase agreement, financing paperwork, and if you have any business use, start that mileage log now! Even a small percentage of business use can add up over time.

Just wanted to add that you should also consider whether you need to make quarterly estimated tax payments if you do this type of event organizing again. Even though you broke even this time, if you organize another event next year and make a profit, you might owe penalties for not paying estimated taxes throughout the year. Also, make sure to save documentation about the non-profit nature of this event - any communications showing your intent was to support the local music scene rather than make money. This can help if the IRS questions whether this should be treated as a business activity or something else. The fact that you actually lost money out of pocket supports that this wasn't profit-motivated. One more tip: if you do get audited, having photos and promotional materials from the event can really help prove it was a legitimate community event rather than just an attempt to create paper losses.

This is really helpful information everyone! I'm dealing with a similar situation from selling handmade crafts at local markets and got a 1099-K that caught me off guard. The advice about using Schedule C even for one-time activities makes sense, especially since the IRS already has that income reported to them. One thing I'm wondering about - for those who mentioned keeping detailed records, what's the best way to organize everything? I have receipts scattered across email, bank statements, and some physical receipts. Should I create a spreadsheet or is there a better system for tracking all these expenses in case of an audit? Also, does anyone know if there are limits on what types of expenses can be deducted? I had some travel costs to purchase materials from suppliers in other cities - would those count as legitimate business expenses even though this was more of a hobby that happened to generate income?

Just went through this exact situation last month! My company filed for Chapter 11 in October and I was panicking about my W-2 too. Here's what actually worked for me: First, I found the bankruptcy court filing online through PACER (Public Access to Court Electronic Records). The filing listed the bankruptcy trustee's contact information. I called their office and they confirmed they're legally required to issue W-2s - they just needed more time to sort through the company's records. While waiting, I also contacted my state's Department of Labor. Turns out they had quarterly wage reports on file for my employer that showed my earnings by quarter. This gave me a backup way to verify my annual income if the W-2 never came. The trustee ended up sending my W-2 in late February, but having those state records gave me peace of mind that I could file accurately either way. Don't panic - there are definitely ways to handle this even when the company completely disappears! Also, keep detailed records of every attempt you make to get your W-2 (emails, phone calls, etc.). The IRS wants to see you made good faith efforts before using Form 4852.

This thread has been incredibly helpful - I'm bookmarking it for future reference! I wanted to add one more resource that might help people in similar situations. If your former company had any kind of employee benefits portal (like through Workday, ADP Workforce Now, or UltiPro), try logging in to see if your year-end documents are available there. Sometimes these systems maintain access to tax documents even after the company shuts down, at least for a short period. Also, check your email for any automated notifications from payroll systems throughout the year - sometimes these emails contain pay stub attachments or links that might still work. I found three months' worth of pay stubs buried in my spam folder from automated payroll notifications. One last tip: if you had health insurance through your employer, contact the insurance company directly. They often have records of your annual wages since premiums are typically calculated as a percentage of income. My health insurer was able to provide a letter showing my reported annual salary, which helped validate my Form 4852 calculations. Really grateful for everyone sharing their experiences here - it's making a stressful situation feel much more manageable!