Best Answer: You should use one of the online filing services listed at irs.gov; compare them to find the best-priced (but do not use TaxSimple; simple it is NOT). There's a questionnaire to find which ones you qualify for. Some of them also offer state filings. And, if you visit your state's department of revenue/taxation site, you may well find that you can file both state and federal for free if you go that route. Just compare both site's offerings.
You answer questions providing the totals you paid for medical insurance premiums, doctors' visits, and prescriptions. All those things are deductible if they exceed a set percentage of your income; the online tax-preparing service will compare your itemized deductions against the standard deduction and file whichever way will get you back the most money. From what you say, it sounds like you could get a big chunk back
if you paid out a lot for medical expenses.
If you own property, you can claim the real estate taxes paid and the interest paid on the mortgage; that always adds up to a lot.
If you have stocks and bonds or mutual funds and keep a safe deposit box for the certificates, you can claim the box rental as an investment cost.
You want to keep all your receipts for at least 3 years, and declare all Forms 1099, etc. By the way, Form 1099-B (for loss or gain on securities sales) is very misleading; you actually put it on Schedule D; you don't list it in the area where online services ask about Forms 1099.
Source(s): Online filer for more than 5 years; secretary to tax lawyer (at one time in the past) for 10 years.
L.G. · 8 years ago