Organizing for Taxes

How can I reduce the stress of preparing to file my taxes? I dread tax time. There has to be a better way to prepare.

I dread The Ides of April. Just thinking about preparing my tax return and dealing with my accountant makes me anxious. Because I dislike organizing complex financial information and papers, I worry that I haven’t saved statements or receipts that would be beneficial to me tax-wise. I wind up feeling overwhelmed and at the mercy of my accountant who can’t help but pressure me for more detailed information. I’m very fortunate to have inherited from my parents, and I am an active philanthropist. But because numbers and papers are stressful for me, I can easily miss details relating to my real estate income and the deductions I am entitled to claim for my charitable gifts and medical expenses. I’m confident in all other areas of my life, but I need someone I can trust to help me prepare for tax time and to get it all done correctly and seamlessly.

The Dilemma

  • A woman of independent means and lifestyle for whom financial matters were a source of stress and upset
  • Taxes, in particular, made her feel nervous and pressured
  • An active philanthropist, she did not understand which documents were important and, as a result, kept everything and could find nothing
  • Medical claims were not filed or tracked on a regular basis
  • Real estate investment records were disorganized
  • Drawers and boxes jammed full of duplicate and irrelevant papers.
  • Medical expenses were not fully reimbursed by insurance and the unreimbursed portion was not tracked or claimed on her tax return
  • Difficulty communicating with real estate managers regarding her investment properties and income
  • Tax returns routinely filed on extension so the stress of preparing for taxes continued throughout the year

The OSI Solution

  • Client meets with OSI twice per month to review incoming mail and bills
  • OSI has streamlined bill payment, makes bank deposits and manages domestic payroll
  • Custom QuickBooks file tracks all spending in tax relevant categories
  • OSI organizes materials for tax preparation year-round and provides reports and materials to client’s accountant; tax returns are now routinely filed before April 15th
  • Estimated income tax and real estate tax obligations are monitored and paid ahead of schedule; cash draw-downs are coordinated with the client’s wealth advisor
  • OSI submits client’s medical claims and tracks unreimbursed medical expenses throughout the year
  • The client’s financial life is on autopilot, reducing the client’s stress about paying her bills and filing her tax returns
  • Physical files are maintained and purged annually so the client can easily find what she needs
  • OSI works with the client’s tax preparer and provides reports and document backup needed for the early filing of returns
  • Client’s annual unreimbursed medical expenses are documented for tax purposes

OSI Tax Organization Services can also include:

  • Setting up online tax payment capability
  • Annual tracking of deductible expenses
  • Coordination with client’s accountants and other financial professionals
  • Organization of tax filing materials annually and year-round
  • Scheduling and planning for property tax and quarterly personal estimated tax payments