Another option to consider is asking your employer for a salary increase instead of direct reimbursement. I did this successfully by creating a detailed presentation showing: 1) Market rates for our position with these skills 2) How these skills would directly benefit our department 3) Specific projects where the training/software would make immediate impact My director couldn't approve the training costs directly due to budget rules, but was able to process a 5% "skill adjustment" to my base salary. This actually worked out better since it's permanent rather than one-time reimbursement. Might be worth trying if traditional reimbursement isn't available in your department.

Has anyone tried negotiating for comp time instead of direct payment for training? My department also has zero budget for training, but my supervisor approved me taking a 2-day software course during work hours and counting it as regular work time. Technically, I still paid for the course myself, but not having to use PTO was worth about $350 in equivalent salary. Might be a partial solution if your manager has time approval flexibility even without budget authority.

Former restaurant manager here. This happens way too often because payroll systems for restaurants are notoriously bad at handling tip pools correctly. Here's what should happen: 1) Server reports total tips received 2) Server reports tip outs to support staff 3) Server is only taxed on tips retained 4) Support staff report and pay taxes on their share Most POS systems track this, but many payroll processors don't implement it correctly. If your manager won't fix it, document everything and talk to the owner. This is actually costing them money too since they pay employer payroll taxes on inflated wages.

This happened at every restaurant I've worked at. The worst part is when tax time comes and the IRS thinks you made WAY more than you actually did! Has anyone successfully gotten this fixed retroactively? Like for previous tax years?

To answer your original question - a GOOD tax preparer should be finding you every legitimate deduction you qualify for while keeping everything accurate and documented. It's not an either/or situation. My accountant helped me deduct about $4200 more than I thought possible when I started my small business, but she also insisted on proper documentation for everything. She explained that aggressive but legitimate deductions are fine, but we need records to back everything up. The real value isn't just in finding deductions - it's in their knowledge of what's allowed, what requires special documentation, and what might trigger audits. Anyone promising huge magical deductions without talking about documentation is probably sketchy.

I actually switched from a "find every deduction" guy to a more conservative preparer after getting audited three years ago. My old preparer found me tons of deductions but didn't explain what documentation I needed. When I got audited I was completely unprepared. My new accountant is super thorough and explains everything. She still finds deductions but is careful to make sure I understand what records to keep. I actually get roughly the same refund amount but with WAY less anxiety. Good tax prep isnt about being aggressive or conservative - its about being THOROUGH and KNOWLEDGEABLE. Good preparers know exactly where the lines are and help you get every benefit you're entitled to without crossing those lines.

The limited definition problem extends beyond just progressive taxation. I teach economics, and textbooks routinely oversimplify tax concepts to make them easier to teach, which unfortunately gets repeated everywhere. Real-world tax systems are incredibly complex with multiple overlapping philosophies. For example, the US corporate tax system has elements of: 1) Income-based progression (higher rates on higher income) 2) Industry-specific rates (differential taxation) 3) Behavior-based incentives (R&D credits, etc.) 4) Profit-rate considerations in certain cases But students only learn the basic "tax rate increases as income increases" definition, which gets repeated throughout their education and careers. It's similar to how we teach supply and demand curves as always being straight lines when they rarely are in reality.

I actually wrote my dissertation on this exact topic! The reason "progressive taxation" is so narrowly defined is because of a deliberate political choice in the early 20th century. When modern income tax systems were being developed (1910s-1930s), there were competing proposals for progressive taxes based on wealth, land value, corporate profit rates, and income. The income-based approach won out partly because it was easier to implement with the administrative capabilities of the time, but also because it was less threatening to accumulated wealth. A progressive wealth tax would have directly challenged the existing power structures more than income taxes. By focusing the definition of progressive taxation exclusively on income, it shifted the burden to high-income earners while protecting those with substantial accumulated wealth. This definition then became codified in academic literature, policy discussions, and eventually public understanding.

One thing nobody's mentioned yet - if you reinvest in another property as your primary residence, you might be able to use the Section 121 exclusion in the future. Won't help with the depreciation recapture specifically, but might save you on other capital gains in the future. Also, check if you have any suspended passive losses from the property that could offset some of the recapture income. Sometimes if you couldn't take passive losses in previous years due to income limitations, they get suspended until you dispose of the property.

Has anyone used a cost segregation study to minimize the depreciation recapture hit? I did this on my last property and it seemed to help, but I'm not sure if it was worth the cost of the study.