Trust This. | By Joseph E. Seagle, Esq. | 👋 Happy Friday! The Legislature just handed the property tax decision to you. November is closer than it looks — and the local-government rewiring starts now, ballot or no ballot. |
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| | 1 big thing: Florida lawmakers send property tax overhaul to November ballot | | On Tuesday, the Florida House (75-26) and Senate (30-9) passed Gov. Ron DeSantis' property tax overhaul. If 60% of voters approve the constitutional amendment in November, the state's homestead exemption climbs from $50,000 to $150,000 on January 1, 2027, and to $250,000 a year later — wiping out property taxes for roughly 60% of Florida homeowners on day one and reaching 92% at full phase-in. | Why This Reshapes Florida's Fiscal Landscape | Property taxes are the operating engine of every Florida city and county. Florida has no income tax, and the constitution forbids one. A House bill analysis cited an estimated $8.4 billion annual hit to local governments at full phase-in. Lawmakers already stripped the state trust fund DeSantis proposed as a backstop, which means cities and counties are on their own. | Manatee County Commissioner George Kruse spelled out what that looks like in practice: bus fees, boat-launch fees, park fees, and longer service lives on police cruisers. Bartow has already shelved a public aquatic center on the news. Joel Berner, senior economist at Realtor.com, warned that when public services degrade, home values follow them down. Public services are baked into the price. | What to Execute and Watch | For home services businesses — HVAC, plumbing, electrical, painting, roofing — expect fee-funded permitting and inspection regimes to replace tax-funded ones. Build pricing flexibility into 2027 estimates and watch for new municipal franchise charges in your operating counties. For real estate investors and private lenders — non-homestead and out-of-state buyers absorb a larger share of the local tax base by design. Underwrite for higher non-homestead millage in all counties, especially Palm Beach, Miami-Dade, and Broward, and for service-degradation risk in Manatee, Sarasota, and rural Panhandle counties. If local services degrade, property values could suffer. For licensed professionals — physicians, dentists, attorneys — homestead-exempt clients will redirect cash flow toward private services (security, schools, healthcare, and alternative dispute resolution services to avoid overburdened and unfunded local courts) that public budgets stop covering. Position for it.
| The Bottom Line | The decision is now in voters' hands, but cities and counties are already pricing in the loss. The legal architecture of Florida ownership — what's homestead, what's titled where, what's in a trust — matters more in a property-tax-less Florida than it did in a property-tax-heavy one. | Watch for: Florida TaxWatch's June analysis, county-by-county fee proposals before October budget cycles, and the November ballot language fight — Sen. Lori Berman's "real description" amendment failed, so the language voters see will be the legislative draft. |
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| | 2. HB 1337 quietly modernizes probate on July 1 | | While the property tax fight grabbed headlines, the Florida Legislature delivered a meaningful probate update earlier this session. CS/HB 1337, signed April 30 as Chapter 2026-57, takes effect July 1, 2026 — and it changes the math for thousands of estates. | Why it matters | Florida probate has been operating on small-estate thresholds set decades ago when a dollar was worth a lot more. HB 1337 finally raises the ceiling to deal with the inflation that has occurred since then. The bill doubles the cap on summary administration from $75,000 to $150,000, doubles the disposition-without-administration cap on intestate personal property from $10,000 to $20,000, and raises the maximum income-tax refund a surviving spouse or child can claim without opening probate from $2,500 to $5,000. Bank-held funds payable to family without administration doubles from $1,000 to $2,000. | What changes in practice | A surviving spouse with a $140,000 brokerage account and a paid-off Honda no longer needs a full formal administration in Probate Court. Summary administration — fewer filings, faster distribution, lower legal fees — now reaches that estate. The bill also lets a personal representative force banks to open a decedent's safe deposit box on presentation of letters of administration, and authorizes a personal representative to initiate enforcement proceedings with mandatory fee shifting. | For home services and licensed professionals — the death-of-a-spouse client conversation gets simpler for a much larger slice of your customer base. Fewer estates will need full administration before insurance, vehicle titles, or business interests can be touched. | For real estate investors — small inherited estates with one rental and modest cash often slipped through formal administration purely because of the $75,000 threshold. The new ceiling reroutes many of those through summary administration, which closes faster and costs less. | The Florida Takeaway | These are not glamorous numbers, but they are the numbers that decide whether a grieving family hires a probate attorney for six months versus three weeks. The thresholds had drifted out of line with current asset values. July 1, they snap back. Would have been nice if the Legislature had built in automatic-escalation clauses based on inflation so they don’t have to do this every decade. | What's Next: If you have clients with estate plans built around the old summary-administration cap — or family bank account workarounds — those documents should be reviewed before the change lands. (For non-Florida readers: HB 1337 is Florida-only. Your state's probate thresholds operate under separate statutes.) |
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| | | If you missed the live stream of Wednesday evening’s “Ask Joe” podcast where I answered questions from the audience, fret not. The recording of the podcast is available for free at any time on our YouTube channel along with other easily accessed channels. | Listen in or watch on your favorite streaming platform. |
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| | 3. The Gift Tax myth that costs Florida families real money | | Most Florida business owners and real estate investors believe two things about the annual gift tax exclusion that aren't quite right — and that misunderstanding is the single most common reason they fail to move wealth efficiently while they're still alive. | The big picture: Crossing the $19,000 annual exclusion does not mean writing a check to the IRS. It almost always means filing Form 709 as a paperwork exercise, with no actual tax owed until you've burned through your $15 million per-person lifetime exemption (or $30 million per couple). | Why it matters: | "I can only give $19,000" leaves significant wealth-transfer capacity on the table every year you're alive Probate transfers are public, slow, and expensive; lifetime transfers are private, fast, and often free Florida's homestead and creditor-protection statutes don't help wealth that ends up stuck in a probate court because it never got moved Entrepreneurs who are pushing against the estate tax cap can gift chunks of their business stock, membership interests, and land trust beneficial interests into irrevocable trusts for children before the assets increase in value through appreciation or a liquidation event (i.e. a sale to private equity), shielding more value from taxation.
| What most people don't know: Four strategies routinely move large sums tax-free and, in most cases, report-free. | Key takeaways: | Split gifts with a spouse — combine two annual exclusions to give $38,000 per recipient per year; or $76,000 from one married couple to another married couple. No Form 709 if the funds come from a joint account; one Form 709 to elect the split if from an individual account. A great way to reduce a taxable estate that’s just over the line. Superfund a 529 plan — front-load five years of exclusions in one transfer: up to $95,000 per beneficiary ($190,000 for married couples). Requires one Form 709 to make the 5-year election, then nothing for the next four years. Bonus: the funds leave your taxable estate. Pay schools and medical providers directly — unlimited tax-free transfers for tuition or medical bills, with no exclusion impact, no reporting, no lifetime exemption use. The check must go to the institution, not the person. Cascade across a family unit — a married child with two grandchildren is four recipients. You and your spouse can move $152,000 per year, report-free, into that household alone.
| Where people go wrong: Writing the check to the patient instead of the hospital. Reimbursing tuition instead of paying the school directly. Using a joint-account workaround without confirming the account is actually joint. Treating Form 709 as a "tax bill" rather than what it is — a recordkeeping return that nibbles at a multi-million-dollar lifetime exemption. | The bottom line: The federal gift tax rules favor people who plan. They penalize people who default to "I'll just leave it in the will." Probate is the slowest, most public, and most expensive way to move money. Direct payments and superfunded 529s are the opposite. (Florida-specific note: state gift tax — none. Federal rules govern. Florida's land trust, LLC, and homestead protections layer on top of the federal transfer framework, not in place of it.) | Go deeper: Read the full long-form article on aspirelegal.com, and download this week's Florida Family Gifting Decision Guide (free PDF) for the four strategies plus the Form 709 decision tree. |
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| | 4. Pick three buckets — or your business picks for you |  | The only thing on Hudson and Edward’s bucket list is napping at 3:00 every day. |
| Most entrepreneurs spend Monday morning reacting to whichever urgent thing landed first. Then they spend Friday wondering why the week didn't move the business forward. The pattern isn't a discipline problem. It's a prioritization architecture problem — and the fix is older than EOS. | The Big Idea: Your business has exactly three buckets | Successful operators run their week against three growth buckets — not five, not seven. The rule is structural: | One bucket focused on revenue generation (new client acquisition, pipeline, conversion) One bucket focused on working on the business, not in it (systems, SOPs, delegation infrastructure) One bucket focused on customer journey or lifetime value (onboarding experience, retention, repeat engagement)
| Anything that doesn't fit into one of those three buckets is, by definition, not a growth activity this quarter. Some of it still has to get done. None of it deserves your best hours. | Why this turns into leverage | This isn't a productivity hack. It's an EOS-compatible filter. Your quarterly Rocks should map cleanly onto the three buckets. Your Accountability Chart should make it obvious who owns each bucket day-to-day. Your Level 10 meeting scorecard should track the leading indicators in each. When a new opportunity lands on your desk, the question is no longer "is this good?" The question is "which bucket does this serve, and at what cost to the other two?" | Where founders get stuck | Picking three buckets that are all "in the business" — three flavors of execution, no time spent designing the company Treating it as a one-time exercise instead of the lens you apply every Monday Hiding behind delegation — naming buckets, then doing all the work in them yourself
| Bottom Line: Your great-at and your love-to-do are the same shortlist. The three buckets sharpen the shortlist into a strategy. Everything outside the buckets is a candidate for delegation, automation, or deletion. | This Week's Challenge: Write your three buckets on a single index card. Tape it to the wall above your monitor. For one week, every task you say yes to has to name the bucket it serves — out loud, to yourself, before you accept it. Notice how many tasks fail the test. |
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