Each tax year, you may be required to fill out Form 5500, depending on the type of plan you choose. SEPs1 are one of the most common retirement savings plan options for 1099 workers.Popular choices include SEP IRAs, SIMPLE IRAs and solo 401(k)s, each offering distinct benefits and contribution limits. IRS Form 1099-R is provided to all Florida Retirement System benefit recipients before January 31st every year. If You Return to FRS Employment. If you need to file a Form 5500 or 5500-SF, please visit our EFAST2 Filing website. The Pension Benefit Guaranty Corporation can answer your questions about defined benefit plans. Reportable disability payments made from a retirement plan must be reported on Form 1099-R. 457b Roth payroll contributions are made on a post-tax basis and give you more flexibility when it comes to meeting your retirement income goals. Small business owners often think they can't afford to offer a 401(k) plan.