Tax Strategies
Sterling analyzes 56 Tax topics against every household.
| Topic | What it does |
|---|---|
| 529 Plan to Roth IRA Conversion | Identify eligible 529 plans and recommend annual rollovers to the beneficiary's Roth IRA under SECURE Act 2.0. |
| ABLE Account | Evaluate ABLE-account eligibility and funding for tax optimized contributions and growth. |
| Asset Location | Evaluate asset location across taxable, pre-tax, and Roth accounts and emit balanced sell+buy directives to relocate holdings into their tax-optimal wrapper. |
| Augusta Rule | Identify Augusta-Rule (IRC §280A(g)) opportunities — researched fair-market rent and an estimated annual tax saving for households with a business and primary residence. |
| Business Expense Deductions | Surface commonly-missed business deduction categories for self-employed and small-business owner households. |
| Capture Primary Residence Exemption | Flag IRC §121 exclusion deadlines for former primary residences and recommend sale-timing review. |
| Client Backdoor Roth IRA Contribution | Identify the client's backdoor Roth opportunity and emit the contribute-then-convert directive pair when MAGI is above direct-Roth limits and the pro-rata trap is clear. |
| Client FSA Contribution | Recommend the client's Healthcare FSA election sized to projected qualifying medical expenses, current year only. |
| Client Roth IRA Contribution | Emit annual transfer directives funding the client's Roth IRA up to the contribution limit, with age-50 catch-up where applicable. |
| Client Traditional IRA Contribution | Emit annual transfer directives funding the client's Traditional IRA up to the contribution limit when the deduction is available and Roth is not. |
| Conservation Tax Credit Purchase Strategy | Surface the opportunity to buy transferable state conservation-easement tax credits covering the full state liability at a discount, and model the net state-tax savings (about 10% of credits purchased) in each credit-offering-state year. |
| Cost Segregation Analysis | Flag households with rental real estate that should consider a cost-segregation study to accelerate depreciation. |
| Cross-Generational Roth Strategy | A backdoor way for adult children to contribute beyond normal Roth limits via gifting to their parents to pay for the parent's Roth Conversions. |
| Deduct Assisted Living Expenses | Identify potential medical-expense deductions for assisted living when expenses exceed the 7.5% AGI threshold. |
| Deduct Medical Expenses | Analyze medical expenses for Schedule A deduction when expenses exceed 7.5% of AGI and itemized > standard. |
| Employee Retirement Contributions (Client) | Maximize the client's elective deferral into their employer retirement plan, layering age-50 and SECURE 2.0 age 60–63 catch-ups. |
| Employee Retirement Contributions (Spouse) | Evaluate the spouse's elective deferral into their employer plan and emit tiered transfer directives — base, age-50, and age 60-63 enhanced catch-up — to bring the spouse to the federal annual limit through retirement. |
| Extra Withholding for Penalty Avoidance | Use a 100% withholding IRA draw with a 60-day rollover to cure underpayment penalties, treated as paid evenly across the year. |
| File Form SSA-44 to Reduce Medicare Premiums | Identify Medicare-eligible household members whose IRMAA surcharge could be reduced by filing Form SSA-44 after a Life-Changing Event. |
| Flexible Spending Account (FSA) | Recommend healthcare and dependent-care FSA elections sized to projected qualifying expenses, current-year only. |
| Gifting for Step-Ups | Gift low-basis appreciated assets to a parent or grandparent so they receive a date-of-death basis step-up and pass back to the household, or down to the next generation, free of the accumulated capital gain. |
| Hire the Spouse | Flag the hire-the-spouse strategy for business-owner households where the spouse can legitimately work in the business. |
| HSA Contributions | Maximize HSA contributions for the household during their eligible years. |
| HSA Deferral | Confirm whether the household has the cash flow to pay current medical expenses outside the HSA and to defer HSA reimbursements for decades to maximize tax-free compounding. |
| Inherited RMD Requirements | Explain the RMD obligations on inherited retirement accounts under SECURE 2.0 rules and the distribution-smoothing levers. Advisory-only — the engine already models the required schedule, so no directives are emitted. |
| IRMAA Monitoring | Monitor household proximity to IRMAA brackets and flag income-management decisions in the 2-year lookback window. |
| Mega Backdoor Roth (Client) | When the client's 401(k) permits after-tax contributions and in-plan Roth conversions, fill the §415(c) headroom and convert immediately to Roth; emit chained transfer directives sized to that headroom. |
| Mega Backdoor Roth (Spouse) | When the spouse's 401(k) permits after-tax contributions and in-plan Roth conversions, fill the §415(c) headroom and convert immediately to Roth; emit chained transfer directives owned by the spouse, sized to that headroom. |
| Net Unrealized Appreciation | Evaluate whether to use the NUA strategy on low-basis employer stock held inside a 401(k) before rollover or retirement. |
| NIIT Monitoring | Monitor household proximity to the Net Investment Income Tax threshold and surface income-timing decisions. |
| Premium Tax Credit | Identify Premium Tax Credit opportunities and income-management strategies for marketplace-insured households. |
| Property Tax Exemptions | Surface state and local property-tax exemptions the household may qualify for but has not yet claimed. |
| PTET / SALT Deduction Strategy | Identify which pass-through business should make the state's Pass-Through Entity Tax election to work around the federal SALT cap, and estimate the entity income, PTET, and federal tax savings. |
| QBI Deduction Maximization | Evaluate whether the household's §199A QBI deduction can be expanded through income management, wage/property tests, or entity choice. |
| Qualified Charitable Distributions | Direct IRA distributions to qualified charities for donors 70.5+, satisfying RMDs while excluding the distribution from AGI. |
| Qualified HSA Funding Distribution | Identify the once-per-lifetime IRA-to-HSA transfer opportunity and emit the funding directive when advantageous. |
| Report Treasury Interest | Confirm that Treasury interest in taxable accounts is being excluded from state taxable income on the state return. |
| Required Minimum Distribution (RMD) | Explain the RMD obligation and optimization levers for household members at or approaching RMD age. Advisory-only — the engine already models the RMD stream, so no directives are emitted. |
| Rollover Traditional IRA to 401(k) | Explain when a reverse rollover of Traditional IRA assets into the employer 401(k) is worthwhile. Advisory-only — the engine treats IRA and 401(k) balances identically, so no directive is emitted. |
| Roth IRA Conversion | Sweep every conversion breakpoint with the cash-flow engine and recommend the bracket-fill schedule that maximizes long-run net legacy value. |
| Roth IRA Conversion for Parents | Surface a multi-generational Roth-conversion opportunity when parents are in a lower tax bracket than the household and the household is the likely heir. |
| Roth IRA Fees from Taxable Accounts | Confirm that Roth IRA advisory fees are paid from a taxable account, preserving tax-free Roth growth. |
| S-Corporation Wages and K-1 Split | Evaluate whether a self-employed household or business owner would save more in self-employment/FICA tax by electing S-Corp treatment than it would cost to administer the S-Corp. |
| Saver's Credit | Identify household members who may qualify for the Saver's Credit and ensure it is claimed on the tax return. |
| SEP/SIMPLE IRA Employer Tax Credit | Surface the SECURE Act small-employer plan-startup tax credit available when a small business establishes a new SEP or SIMPLE IRA. |
| Small Employer Auto-Enrollment Tax Credit | Explore tax credit available to small employers who add auto-enrollment to their retirement plan. |
| Spousal Backdoor Roth IRA Contribution | Identify the spouse's backdoor Roth opportunity and emit the contribute-then-convert directive pair when MAGI is above direct-Roth limits and the spouse's pro-rata exposure is clear. |
| Spousal Roth IRA Contribution | Emit annual transfer directives funding the spouse's Roth IRA up to the contribution limit, with age-50 catch-up where applicable. |
| Spousal Traditional IRA Contribution | Emit annual transfer directives funding the spouse's Traditional IRA up to the contribution limit when the deduction is available and Roth is not. |
| Spouse FSA Contribution | Recommend the spouse's Healthcare FSA election sized to projected qualifying medical expenses, current year only. |
| Stacked Charitable Donations | Bunch multiple years of charitable giving into a single tax year to exceed the standard deduction and capture itemized tax benefits. |
| Start Roth IRA Five-Year Clock | Emit a createAccount + minimal seed transfer directive when a household member nearing retirement has never opened a Roth IRA. |
| Tax Gain Harvesting | Identify households with 0% long-term-capital-gains bracket capacity who could realize appreciated taxable gains at no federal tax cost. |
| Tax Loss Harvesting | Emit a sell+buy directive pair for each harvest-eligible loss position in taxable accounts, with wash-sale awareness. |
| Tax-Efficient ETF Replacement | Identify high-turnover, capital-gain-distributing mutual funds in taxable accounts and recommend equivalent ETF replacements where the after-tax benefit outweighs the switching cost. |
| Zero Income State Tax Roth Conversion | Evaluate whether a temporary or permanent relocation to a zero-income-tax state for a large Roth conversion year would save meaningful state tax. |