Self-Employment Insurance & Tax Setup

Flexible on price, just putting the lowest for starters. I’m newly self-employed and want a coordinated plan that covers three tightly linked needs: selecting private health insurance for my wife, our new baby, and myself. How to structure our finances so those premiums (and other costs) are fully deductible, and filing our federal and state returns when tax season arrives. The objective is to lower our taxable income—and with it our student-loan payments—by leveraging every legal deduction available (insurance premiums, HSAs, SEP or Solo 401(k), etc.). I need to be clear on the exact forms, thresholds, and record-keeping requirements so we stay compliant while maximising savings. Everything can be done through virtual video calls. I’m looking for an initial deep-dive session to set things up, where all of our questions can be answered so we can make a decision on how to proceed. If needed, we could follow up with one or two shorter check-ins as we implement the plan and complete the return. Would be willing to pay more for extra meetings if needed. Deliverables • Roadmap for choosing and enrolling in a qualifying private health plan, with a comparison of at least three viable options. • Written tax strategy that shows where each deduction will appear on Schedule C/Form 1040, how we’ll reduce Adjusted Gross Income for student-loan calculations, and any quarterly-estimated tax needs. • Preparation and e-filing of our next federal and state returns, with full work-paper documentation. • Two post-setup video check-ins to fine-tune the strategy or handle rule changes. A CPA, EA, or seasoned tax professional who routinely helps self-employed clients would be perfect. Familiarity with marketplace insurance rules, Schedule C adjustments, and income-driven repayment calculations is essential. If that’s you, share a brief on similar clients and the tax software you prefer, and let’s lock in coverage and savings well before the next deadline.

Project ID: 40569907