Experienced CFP/CPA Needed: Multi-Stream Tax Reduction, Fed Retirement & Small Business Strategy

Posted 3 weeks ago

Only freelancers located in the U.S. may apply.U.S. located freelancers only

Summary

I am a GS-13 federal employee (age 62, approaching retirement eligibility) and the sole owner of an active Virginia S-Corporation holding a federal government contract. I am also a practicing fine artist with emerging institutional income and an active residential property held in an LLC. I need a seasoned Certified Financial Planner or CPA-level tax strategist who can look across all of my income streams simultaneously and architect a cohesive, integrated strategy — not manage a single piece of the puzzle. My situation is genuinely multi-layered and requires someone comfortable holding complexity: • Federal retirement: FERS pension, TSP rollover strategy, Social Security (age 62 claim, WEP/GPO resolved under Social Security Fairness Act), and OPM coordination • S-Corporation: Active federal contract income flowing through an S-Corp (Form 1120-S filed annually); need ongoing officer compensation optimization, QBI deduction maximization, retirement vehicle strategy (prior SEP rolled into TSP; no Solo 401(k) currently established), Section 179 planning, and accountable plan documentation • Real estate: Residential condo held in an LLC, currently evaluating mortgage recast, rental conversion, depreciation strategy, and Real Estate Professional Status (REPS) — specifically whether REPS is defensible and beneficial given anticipated post-retirement income structure • Tax liability reduction: I need specific, executable strategies — not general guidance — covering the transition years between active federal employment and full retirement, when S-Corp income, pension, Social Security, and rental income all overlap • Future income: Emerging fine art income (institutional commissions, auction houses) that will eventually need its own tax treatment and estate integration • Ongoing continuity: I want someone who can work with my existing CPA (tax filing) and estate attorney without duplicating effort, taking a CFP-level planning role that neither currently fills WHAT I AM NOT LOOKING FOR • General financial wellness coaches • Advisors who only manage investment portfolios and collect AUM fees • Anyone who will redirect me back to a generalist or suggest I "talk to a CPA" — I have one • Template advice that does not engage with federal employee benefit structures specifically IDEAL BACKGROUND • CFP credential strongly preferred; CPA with retirement planning depth considered • Demonstrated experience with federal employee retirement (FERS, CSRS, TSP, OPM processes) • Hands-on S-Corporation tax strategy experience (not just bookkeeping) • Familiarity with real estate professional status (REPS) qualification and documentation • Ability to model multi-income-stream scenarios across a 3–5 year retirement transition horizon • Estate-aware thinking (LLC, S-Corp, and estate attorney already engaged) • Comfortable working alongside existing advisors as a planning coordinator, not a replacement • Patient, clear communicator — able to explain complex strategies in plain language and take time to ensure full understanding before moving to execution SCOPE OF ENGAGEMENT Phase 1 Review of existing financial documents, retirement projections, S-Corp structure, and real estate scenarios. Produce a prioritized tax reduction and retirement income strategy document with specific, actionable recommendations. Phase 2 (Ongoing — as needed): Quarterly check-ins, year-end tax planning coordination, S-Corp officer comp and distribution review, and as-needed consulting on real estate and art income decisions. BUDGET Open to discussion. Prefer hourly for Phase 1 with potential to establish a retainer for ongoing advisory. Please provide your hourly rate with your application. HOW TO APPLY Please respond with: 1. Your credential(s) and relevant specializations 2. A brief description of 1–2 engagements where you navigated a similar multi-stream situation (federal employee + small business, or federal employee + real estate) 3. Your approach to working alongside an existing CPA and estate attorney 4. Your hourly rate Applicants who send generic proposals without addressing the specifics above will not be considered. This is a U.S.-based engagement. Candidate must have working knowledge of U.S. federal employee benefits, IRS S-Corporation rules, and Virginia/Maryland/DC tax environment preferred.

  • Less than 30 hrs/week
    Hourly
  • 1-3 months
    Duration
  • Expert
    Experience Level
  • $100.00

    -

    $150.00

    Hourly
  • Remote Job
  • Ongoing project
    Project Type
Skills and Expertise
Mandatory skills
Financial Modeling
Financial Analysis
Activity on this job
  • Proposals:10 to 15
  • Last viewed by client:2 weeks ago
  • Interviewing:
    4
  • Invites sent:
    1
  • Unanswered invites:
    1
About the client
Member since Dec 7, 2021
  • United States
    Aldie1:01 PM
  • $12K total spent
    19 hires, 0 active
  • 265 hours
  • Individual client

Explore similar jobs on Upwork

Business Plan
Market Research
Business Modeling
Data Analysis
Financial Analysis
Forecasting
Financial Analysis
Business Valuation
Real Estate Financial Modeling
Pitchbook
Financial Modeling
Business Presentation
Pitch Deck
Microsoft PowerPoint
Microsoft Excel
Business Plan
Graphic Design
Presentations
Market Research
Financial Analysis & Valuation

How it works

  • Post a job icon
    Create your free profile
    Highlight your skills and experience, show your portfolio, and set your ideal pay rate.
  • Talent comes to you icon
    Work the way you want
    Apply for jobs, create easy-to-by projects, or access exclusive opportunities that come to you.
  • Payment simplified icon
    Get paid securely
    From contract to payment, we help you work safely and get paid securely.
Want to get started? Create a profile

About Upwork

  • Rating is 4.9 out of 5.
    4.9/5
    (Average rating of clients by professionals)
  • G2 2021
    #1 freelance platform
  • 49,000+
    Signed contract every week
  • $2.3B
    Freelancers earned on Upwork in 2020

Find the best freelance jobs

Growing your career is as easy as creating a free profile and finding work like this that fits your skills.

Trusted by

  • Microsoft Logo
  • Airbnb Logo
  • Bissell Logo
  • GoDaddy Logo