Annual Retirement Planning Playbook
Scott & Courtney — Early Retirement 2028
Last updated: April 2026 | Review annually each January
Quick Reference: Key Thresholds
| Threshold | 2026 Value | Grows At | Why It Matters |
|---|---|---|---|
| ACA cliff — family of 4 (2028–2036) | $128,600 | ~2.5%/yr (FPL) | Hard subsidy cutoff. HH4 while claiming Aspen (b. July 2018) |
| ACA cliff — family of 3 (2037–2051) | ~$129,000 est. | ~2.5%/yr (FPL) | Aspen ages off at 18 (July 2036). HH3 = Scott, Courtney, Maeve |
| 0% LTCG bracket top (MFJ) | ~$94,050 | ~2.5%/yr | Realize Miller/Schwab gains tax-free below this |
| 12% ordinary bracket top (MFJ) | ~$94,300 | ~2.5%/yr | Optimal Roth conversion zone — sweet spot |
| 22% bracket begins (MFJ) | ~$94,300 | ~2.5%/yr | Conversion cost escalates here |
| IRMAA Tier 1 (MFJ) | ~$206,000 | ~2%/yr | Medicare premium surcharge — relevant from 2049 |
| Colorado Premium Assistance | $138/mo family of 4 | TBD | State subsidy stacks on federal APTC |
| RMD age | 73 | N/A | Forced pre-tax distributions begin |
| Medicare eligibility | Age 65 | N/A | End of ACA window (2051) |
| SS — Courtney FRA | ~Age 67 | N/A | 2053 claiming target |
| SS — Scott max delay | Age 70 | N/A | 2056 claiming target |
| ACA enrollment deadline (CO) | December 15 | N/A | Per OBBBA — no longer Jan 15 |
Phase Overview
| Phase | Years | Ages | Primary Focus |
|---|---|---|---|
| 1 — Pre-Retirement | 2026–2027 | 40–41 | Maximize contributions, plan home sale, bridge coverage |
| 2 — Early Conversion | 2028–2032 | 42–46 | Courtney 401k conversions, ACA cliff management, Miller liquidation |
| 3 — Mid-Window | 2033–2042 | 47–56 | Shift to 457b + Rollover IRA conversions, dividends declining |
| 4 — Late Window | 2043–2050 | 57–64 | Final conversions, 0% LTCG harvesting, IRMAA prep |
| 5 — Medicare Transition | 2051 | 65 | Medicare enrollment, ACA cancellation |
| 6 — SS + Medicare | 2052–2060 | 66–74 | Courtney SS (2053), Scott SS (2056), RMD prep |
| 7 — RMD Era | 2061+ | 75+ | RMD management, estate distribution |
The Annual Calendar
JANUARY — Reset & Plan
Jan 1–5: ACA Coverage Confirmation
- Log into Connect for Health Colorado — confirm January 1 coverage is active
- Verify the correct premium was withdrawn from your checking account
- Confirm the APTC advance amount matches your income enrollment projection
- If household composition changed (child aged off, etc.): call Connect for Health CO immediately
- Phase note 2028–2036: HH4 on tax return (Scott, Courtney, Maeve, Aspen). Aspen covered by Kaitlyn's insurance.
- Phase note 2037–2046: HH3 (Aspen turns 18 July 2036). Maeve ages off at ~2046.
Jan 1–15: Annual MAGI Planning Session
- Open a clean MAGI tracker spreadsheet for the year
- Input projected dividends: pull trailing 12-month actuals from Miller Stock Account and Schwab Stocks
- Calculate: ACA cliff for current year = last year's cliff x 1.03 (approximate)
- Calculate: available Roth conversion headroom = cliff - projected dividends - $3,000 buffer
- Set your "not-to-exceed" MAGI target for the year — write it down
- Phase 2028–2032: Primary vehicle = Courtney 401k. Target: ~$51–65K conversion/year
- Phase 2033–2042: Pivot to Courtney 457b first, then Rollover IRA (Scott), then Sunflower
- Phase 2043–2050: Remaining pre-tax balances; IRMAA watch begins 2049
January: Beneficiary Audit
- Log into every account: Courtney 401k, Courtney 457b, Courtney Backdoor Roth, Fidelity Roth IRA, Charles Schwab Roth IRA, Cvent 401k, Gibbs–Empower, Rollover IRA (Scott), Sunflower–Principal, Miller Stock Account, Schwab Stocks, life insurance
- Confirm primary AND contingent beneficiaries are current
- Update immediately if: new child, death in family, divorce
FEBRUARY — Tax Prep Begins
Feb 1–28: Tax Document Collection
- 1099-DIV, 1099-B, 1099-INT begin arriving mid-February
- Miller Stock Account: expect large 1099-B with proceeds and cost basis detail
- Flag: any Roth conversions from prior year will generate a Form 1099-R
MARCH — Tax Filing
Mar 1–31: Tax Return Preparation
- Critical: verify actual MAGI vs ACA enrollment projection
- If MAGI came in higher: APTC reconciliation means you OWE the difference
- If MAGI came in lower: APTC reconciliation means you get a REFUND
- Verify 0% LTCG bracket was fully utilized on Miller/Schwab dividends
APRIL — File & First Payment
April 15: File Tax Return & Q1 Estimated Tax Payment
- Pay federal estimated tax for Jan–Mar income
- Safe harbor: pay 100% of prior year's total tax liability across 4 equal payments
- Colorado state estimated tax: also due quarterly
MAY — Mid-Year Check
May 15: Mid-Year MAGI Audit
- Tally all income received January–April: Roth conversions + dividends from Miller + Schwab
- Project full-year run rate for dividends
- Recalculate: remaining conversion capacity for May–December
JUNE — Midpoint
June 16: Q2 Estimated Tax Payment
June: Mid-Year ACA Enrollment Review
- Has household composition changed? (Qualifying life event = special enrollment)
- If MAGI tracking meaningfully higher than ACA enrollment projection: update estimate immediately
- Cliff check: If within $8K of cliff, stop all conversions; do final careful conversion in December only
SEPTEMBER — Year-End Setup
September 15: Q3 Estimated Tax Payment
September: Year-End Roth Conversion Decision
- Commit to a conversion target for October–December
- Rule: don't leave more than $5K of headroom unused — that's wasted 12% bracket space
NOVEMBER — Enrollment Month
November 1: ACA Open Enrollment Opens
- Log into Connect for Health Colorado (connectforhealthco.com)
- Do NOT auto-renew without reviewing — plans change every year
- Input next year's projected MAGI accurately
- Enroll before December 15 (Colorado deadline per OBBBA)
DECEMBER — Close the Year
December 15–26: Final Roth Conversion
- Execute the last conversion tranche of the year
- After execution: calculate final actual MAGI — confirm under ACA cliff
December: Final Capital Gains Harvesting
- Last chance to realize gains at 0% LTCG federal rate
- Last chance to harvest remaining losses
One-Time Milestone Events
2027 (Retirement Year)
- [ ] Maximize 401k + 457b contributions through final day of employment (Courtney)
- [ ] Home sale: use $500K married capital gains exclusion
- [ ] Coordinate ACA coverage: qualifying life event (loss of employer coverage)
- [ ] Set up quarterly estimated tax payment system
- [ ] Purchase LTC/hybrid policy before leaving employer
2028 (Year 1)
- [ ] Execute first ACA-optimized Roth conversion: cap at $51K from Courtney 401k
- [ ] Run Boldin Monte Carlo with updated balances — document baseline success rate
2033 (Conversion Pivot)
- [ ] Shift primary Roth conversion vehicle: Courtney 401k -> Courtney 457b
- [ ] Begin Rollover IRA (Scott) conversions simultaneously
2051 (Medicare Enrollment — Age 65)
- [ ] Enroll in Medicare Part A and Part B — submit 3 months BEFORE your 65th birthday
- [ ] Cancel ACA Connect for Health Colorado coverage
2053 (Courtney Social Security at FRA)
- [ ] File for Courtney's Social Security benefit 3–4 months before FRA birthday
2056 (Scott Social Security at 70)
- [ ] File for Scott's Social Security benefit 3–4 months before 70th birthday
2061 (RMD Age — 73)
- [ ] Calculate first RMD for each remaining pre-tax account
- [ ] Goal: pre-tax accounts should be largely converted by this point
Year-by-Year Summary Table
All dollar amounts rounded to nearest $1K. HH4 through 2036 (Aspen claimed), HH3 from 2037+.
KEY UPDATE (April 2026): HH4 gives $30K+ more cliff headroom in 2028–2036 vs old HH3 assumption. Consider increasing early conversions by $20–30K/year.
| Done | Year | Ages | Phase | Conv. Acct | Divs | Conv | MAGI | Cliff | Plan Notes | Your Notes |
|---|---|---|---|---|---|---|---|---|---|---|
| 2026 | 40/40 | Pre-Retirement | n/a (working) | $39K | — | — | Medicare | Update Boldin. LTC planning. Estate docs. | ||
| 2027 | 41/41 | Pre-Retirement | n/a (working) | $47K | — | — | Medicare | RETIRE. Home sale. ACA enroll. | ||
| 2028 | 42/42 | Early Conversion | Courtney 401k | $51K | $51K | $102K | $135K | HH4. $33K unused headroom. | ||
| 2029 | 43/43 | Early Conversion | Courtney 401k | $48K | $57K | $106K | $139K | HH4. | ||
| 2030 | 44/44 | Early Conversion | Courtney 401k | $46K | $63K | $109K | $142K | HH4. | ||
| 2031 | 45/45 | Early Conversion | Courtney 401k | $43K | $69K | $112K | $146K | HH4. | ||
| 2032 | 46/46 | Early Conversion | Courtney 401k | $40K | $75K | $116K | $149K | HH4. | ||
| 2033 | 47/47 | Mid-Window | Courtney 457b | $38K | $82K | $119K | $153K | HH4. PIVOT to 457b. | ||
| 2034 | 48/48 | Mid-Window | Courtney 457b | $35K | $88K | $123K | $157K | HH4. | ||
| 2035 | 49/49 | Mid-Window | Courtney 457b | $32K | $95K | $127K | $161K | HH4. | ||
| 2036 | 50/50 | Mid-Window | Courtney 457b | $29K | $102K | $131K | $165K | HH4. Last year claiming Aspen. | ||
| 2037 | 51/51 | Mid-Window | Courtney 457b | $24K | $111K | $135K | $141K | HH3 begins — cliff drops ~$24K. | ||
| 2038 | 52/52 | Mid-Window | Courtney 457b | $21K | $118K | $139K | $145K | HH3. | ||
| 2039 | 53/53 | Mid-Window | Courtney 457b | $17K | $126K | $143K | $148K | HH3. | ||
| 2040 | 54/54 | Mid-Window | Courtney 457b | $13K | $134K | $147K | $152K | HH3. | ||
| 2041 | 55/55 | Mid-Window | Courtney 457b | $10K | $142K | $152K | $156K | HH3. | ||
| 2042 | 56/56 | Mid-Window | Courtney 457b | $6K | $150K | $157K | $160K | HH3. Miller fully liquidated. | ||
| 2043 | 57/57 | Late Window | Rollover IRA (Scott) | $5K | $156K | $161K | $164K | HH3. | ||
| 2044 | 58/58 | Late Window | Rollover IRA (Scott) | $3K | $164K | $166K | $168K | HH3. | ||
| 2045 | 59/59 | Late Window | Rollover IRA (Scott) | $10K | $114K | $125K | $172K | HH3. | ||
| 2046 | 60/60 | Late Window | — | $8K | — | $8K | $177K | HH3. Maeve college — 529 distributions begin. | ||
| 2051 | 65/65 | Medicare Transition | Medicare begins | $0K | — | — | Medicare | Medicare enrollment. Cancel ACA. | ||
| 2053 | 67/67 | Medicare + SS | n/a | $0K | — | — | Medicare | FILE Courtney SS (FRA). | ||
| 2056 | 70/70 | Medicare + SS | n/a | $0K | — | — | Medicare | FILE Scott SS (age 70). | ||
| 2061 | 75/75 | RMD Era | RMDs (forced) | $0K | — | — | Medicare | RMDs begin. Avoid double-year. |
Document stored in Claude Project for ongoing reference. Update annually each January.