How Tax Moves: 100 Illustrated Lessons
Follow wages, cash transfers, deductions and tax reporting through corporations, partnerships, payroll and property activities.
Read the arrows before moving the money
Solid arrows represent cash where explicitly identified. Dashed arrows represent tax information, classification or review. Each lesson explains the mechanism and its limits. A payment to another entity does not automatically reduce the combined tax bill.
C-Corp Planning
- How does C corporation income tax before an owner takes cash work?
- How does a C corporation dividend and its second tax layer work?
- How does retaining earnings in a C corporation work?
- How does owner payroll as a C corporation expense work?
- How does a C corporation capital contribution work?
- How does equipment purchases inside a C corporation work?
- How does a corporate loan to a shareholder work?
- How does a C corporation business reserve work?
- How does a C corporation loss at the company level work?
- How does the transition from C corporation to S taxation work?
S-Corp Planning
- How does S corporation profit on an owner return work?
- How does S corporation payroll versus distributions work?
- How does an S corporation stock basis increase work?
- How does an S corporation distribution above basis work?
- How does S corporation loss limitation review work?
- How does shareholder funding for business expenses work?
- How does S corporation health insurance reimbursement work?
- How does debt basis when only one shareholder lends work?
- How does an S corporation tax distribution work?
- How does an S corporation shareholder loan repayment work?
Entity Structuring
- How does partnership income from Form 1065 to the partner work?
- How does partnership profit allocation versus cash distribution work?
- How does a guaranteed payment to a partner work?
- How does a partner capital contribution work?
- How does partnership debt in outside basis work?
- How does partnership losses on the partner return work?
- How does a partnership tax distribution work?
- How does participation in a rental partnership work?
- How does reimbursing a partner business expense work?
- How does buying a partnership interest rather than its property work?
- How does a real management fee between two entities work?
- How does related-party pricing in a two-entity arrangement work?
- How does separating property ownership from operations work?
- How does shared payroll cost allocation between entities work?
- How does a royalty between commonly owned companies work?
- How does a loan between commonly owned entities work?
- How does a parent capital contribution to a subsidiary work?
- How does paying a vendor from the wrong entity account work?
- How does a transfer between two commonly owned LLCs work?
- How does owner cash extraction in a two-entity plan work?
- How does an owner loan on the business balance sheet work?
- How does owner equity funding versus a business loan work?
- How does repayment of a loan with reduced debt basis work?
- How does a shareholder guarantee versus a direct loan work?
- How does shareholder loan interest reporting work?
- How does stock basis versus company bank cash work?
- How does a stock contribution before a distribution work?
- How does intercompany loan principal repayment work?
- How does classification of company-paid personal bills work?
- How does a loan schedule in the business return work?
Tax Compliance
- How does the split from gross wages to net pay work?
- How does the employer share of payroll taxes work?
- How does remitting payroll withholding to the IRS work?
- How does payroll for a sole S corporation shareholder work?
- How does a bonus payment through payroll work?
- How does an employee 401(k) payroll deferral work?
- How does employee versus contractor payment classification work?
- How does employee reimbursement versus additional wages work?
- How does paying a spouse through business payroll work?
- How does reconciling Form 941 and W-2 totals work?
- How does estimated tax versus payroll withholding work?
- How does a tax reserve followed by an owner payment work?
- How does a tax safe harbor versus final liability work?
- How does annualized income for estimated installments work?
- How does a rental sale in a new payment projection work?
- How does tax payments during a filing extension work?
- How does a prior-year overpayment applied forward work?
- How does quarterly books in an owner tax projection work?
- How does spouse withholding for joint business income work?
- How does paying an individual final tax balance work?
Rental Property
- How does rental income reporting from tenant to owner work?
- How does a rental mortgage principal and interest split work?
- How does noncash depreciation against rental income work?
- How does depreciation after home-to-rental conversion work?
- How does a rental improvement on the asset schedule work?
- How does rental security deposit accounting work?
- How does vacation rental personal-use allocation work?
- How does a short-term rental loss on the household return work?
- How does property manager fees and net remittances work?
- How does rental sale gain versus net closing cash work?
Retirement Planning
- How does an employer retirement plan contribution work?
- How does a pretax employee salary deferral work?
- How does a Roth 401(k) payroll deferral work?
- How does a cash balance plan funding obligation work?
- How does retirement coverage after hiring employees work?
- How does S corporation salary for retirement contributions work?
- How does a SEP employer contribution work?
- How does retirement coverage across two companies work?
- How does retirement funding alongside business expansion work?
- How does a retirement contribution correction with payroll work?
Business Deductions
- How does an accountable plan reimbursement work?
- How does an owner-paid expense for the correct entity work?
- How does mixed-use vehicle expense allocation work?
- How does the business meal deduction review work?
- How does travel advances and expense reconciliation work?
- How does depreciation versus immediate expensing work?
- How does business interest versus principal repayment work?
- How does an expense correction across business and personal returns work?
- How does home office eligibility before reimbursement work?
- How does preventing duplicate owner reimbursements work?
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