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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
9 proposals
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Active 1 day ago
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9 freelancers are bidding on average $161 USD for this job

As a seasoned Attorney, Advocate, and Legal Consultant, I bring over a decade of experience to the table, specifically in tax compliance and similar matters affecting small businesses and the self-employed. My strong understanding of Schedule C adjustments, income-driven repayment calculations, and marketplace insurance rules will allow me to structure your finances around insurance premiums for maximum deductions and reduced taxable income. In my line of work, precision is crucial. Rest assured that with me there won't be any room for error. I've spent years meticulously reviewing and drafting agreements and legal content ranging from employment contracts to tax returns filings, ensuring every detail is accounted for. In this project, I'll deliver a comprehensive tax strategy indicating where each deduction will appear on Schedule C/Form 1040 while also providing a detailed work-paper documentation. This includes preparing for any potential rule changes or quarterly-estimated tax needs allowing you complete peace-of-mind throughout the journey. So let's leverage my expansive skills and knowledge to ensure you're not just compliant but maximizing your savings well before the next deadline.
$250 USD in 1 day
6.5
6.5

Hi, With over 7 years of experience in tax preparation and financial consulting, I am well-equipped to support your journey into self-employment. I will develop a comprehensive plan that addresses your needs for selecting private health insurance and structuring your finances for maximum tax efficiency. My approach is meticulous; I will provide a detailed roadmap for health plan options and a tailored tax strategy that clearly outlines the deductions available to you, ensuring compliance and clarity in record-keeping. I prioritize clear communication and collaboration, and we will conduct our initial deep-dive session and subsequent check-ins through virtual video calls, allowing for a seamless experience. I will follow all necessary processes to deliver timely, high-quality results while meeting your agreed deadlines. My commitment to accuracy and attention to detail will ensure that you not only maximize savings but also confidently navigate the complexities of tax filing as a self-employed individual. Let’s work together to secure the coverage and financial strategies you need.
$140 USD in 7 days
5.3
5.3

With extensive experience in financial planning, tax optimization, and insurance selection, I understand the importance of creating a comprehensive strategy to maximize savings and lower taxable income. How can we tailor the plan to ensure seamless integration with your current financial situation and future goals? Regards, CA. Swati Jain, CPA
$150 USD in 1 day
4.6
4.6

Hi, I'm Md. Altas Uddin a US tax professional with a valid PTIN and hands-on experience preparing Form 1040, Schedule C and tax returns for self-employed individuals. I help clients maximize eligible deductions, including self-employed health insurance, retirement contributions and other tax-saving opportunities while ensuring full IRS compliance. I can assist with your tax planning, organize the required documentation, prepare and paper work pdf file (not efile) your federal and state returns. To assist reduce your taxable income and support an effective long-term tax strategy. Thank you for your consideration.
$300 USD in 7 days
4.6
4.6

Dear Client, I can help you create a tax-efficient plan as you transition into self-employment. I am a CPA with 15+ years of experience, including Big 4 EY experience, advising individuals and businesses on tax planning, deductions, retirement strategies, and compliance. I can assist with: • Reviewing self-employed health insurance deduction strategies and HSA eligibility • Evaluating SEP IRA/Solo 401(k) options to reduce taxable income • Creating a tax roadmap covering Schedule C, Form 1040, estimated taxes, and record keeping • Preparing federal and state tax returns with supporting documentation I understand the goal is to maximize legal deductions while also considering the impact on student loan calculations. I would start with a detailed consultation to review your situation and provide a practical implementation plan, with follow-up support as needed. Happy to discuss your goals and help you set up the right structure. Best regards, Talha
$250 USD in 7 days
2.7
2.7

There's something about your plan that makes me happy, it is the fact that newly wedded couples are trying to plan and make smart investment decision. I'm going to offer you a refund if you're not satisfied with the service. Moving forward, I'm a legal financial advisor and analyst and I work with one of the biggest insurance company in Nigeria - LEADWAY. I had to state this so you would so you would leverage on my strength for this particular role. As a Nigerian, I will teach you the safest way to play the system legally Let's discuss Sir
$30 USD in 3 days
0.0
0.0

I BELIEVE IN CLIENT RELATIONSHIPS OVER PROFITS. Ethan here, from South Africa. I've read through your project and I'm definitely interested in assisting you. Your project focuses on setting up self-employment insurance and tax structures to maximize deductions and savings. I propose implementing a structured workflow system that includes a detailed analysis of your insurance options and a comprehensive tax strategy outlining deduction placement and compliance requirements. To ensure the highest quality solution, we can start by scheduling a deep-dive video session to address all your queries and set up a clear roadmap. The emphasis will be on understanding your specific needs and tailoring the plan accordingly. What you truly seek is not just insurance and tax setup, but a reliable strategy to lower taxable income and maximize deductions. My approach involves clear communication, a focus on compliance, and delivering tangible savings without overwhelming you with technical jargon. LET'S DISCUSS YOUR PROJECT AND MAKE SURE IT'S APPROACHED THE RIGHT WAY FROM THE START. Kind Regards, Ethan
$100 USD in 8 days
0.0
0.0

Dear Hiring Manager, I am interested in assisting you with your self-employment insurance and tax setup. I have practical experience in bookkeeping, accounting, financial reporting, tax preparation support, bank reconciliations, and maintaining accurate financial records. I am proficient in QuickBooks and Excel and can help organize your financial information, categorize business expenses, prepare supporting schedules, and ensure your records are accurate for tax compliance. I offer: * Accurate bookkeeping and expense categorization * Self-employment income and expense tracking * Financial record organization for tax purposes * Bank and credit card reconciliations * Clear communication and timely project delivery * High attention to detail and confidentiality I am committed to delivering accurate, reliable, and professional accounting support. I would be pleased to discuss your specific tax and insurance requirements and how I can help. Thank you for your time and consideration. I look forward to working with you. Kind regards, Kashif Baig
$140 USD in 7 days
0.0
0.0

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