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PERMITPADDLERHawaiʻi STR Compliance
About · Honolulu, Hawaiʻi

Built in Hawaiʻi. For Hawaiʻi STR owners.

A solo studio operating out of Honolulu — under the Ikena Design & Build umbrella. Same hands that codify USCG maritime compliance into Binnacle AI codified Hawaiʻi STR ordinances into PermitPaddler.

01 — Origin

Why this exists.

I'm a USCG-credentialed captain. I live and work in Hawaiʻi. I run a couple of short-term rentals alongside the captain work — and I ate a late MCTAT filing penalty in March 2026 because I lost track of which county tax was due on which date.

That penalty cost more than a year of PermitPaddler Single. I looked at the existing options — Hostfully, Guesty, Lodgify — and every one of them is a booking platform that bolts on tax tracking as an afterthought. None of them know what an MCTAT is. None know that Maui Bill 9 changed the STRH permit cap in West Maui in 2024. None cite HRS §237D when reminding you about TAT.

So I built the tool I needed. Then I made it work for all four counties — because the only thing harder than tracking six taxes for one property is tracking six taxes per property × thirty properties.

02 — What it is

A four-county compliance ledger.

  • TVR / STRH / NUC / STVR permits, GE Tax, TA Tax, county TAT, smoke detector cert, insurance COI — one calendar per property.
  • Built around a county rule engine. When Maui Council changes the ordinance, I update one file. Every page + reminder updates automatically.
  • Email + SMS reminders at 30 / 14 / 7 / 3 / 1 days before every deadline.
  • Drop a TVR cert PDF — Claude reads it + fills in the dates.
  • iCal feed syncs deadlines to Apple / Google / Outlook (per-property or org-wide).
  • Public read-only API for Enterprise integrations.
  • $79 / $199 / $499 per month. No per-property, no per-user pricing.
03 — What it isn't

A short list, on purpose.

  • Not a booking platform. Use Airbnb / VRBO / FareHarbor. PermitPaddler tracks the compliance side.
  • Not a property manager. You still do the work; we make sure the deadlines don't surprise you.
  • Not a CPA. The audit log + per-filing PDFs make your accountant ~30% faster — but a real CPA still files the return.
  • Not a VC-backed mainland SaaS. No board, no growth-at-all-costs pressure, no plans to pivot to a generic "vacation rental management platform" six months in.
04 — Authorship

One studio. Many tools.

PermitPaddler ships under Ikena Design & Build Group — a solo studio operating out of Honolulu, Hawaiʻi. Ikena (ee-KEH-nah) is Hawaiian for vision. Same person also builds:

  • Binnacle AI — USCG compliance for commercial maritime crews. (binnacleai.com)
  • Hawaii-as-Code — every Hawaiʻi parcel + building + address, as TypeScript + 3D map. (maps.ikenagroup.com)
  • ProBuildCalc, Port of Cams, Property Brief — adjacent Hawaiʻi-rooted tools.

The same county-rule-engine pattern that makes Binnacle work for CFR Part 10/11 maritime crew compliance is what makes PermitPaddler work for STR ordinances. The infrastructure is shared (Vultr, Cloudflare, shared Postgres). The expertise is hard-won — mostly by getting fined first.

05 — What to expect

Operating transparency.

  • Active development. See /changelog. Real fixes ship in hours, not quarters.
  • Real ops transparency. Live DB / reminder cron / integration health at /status.
  • No data lock-in. CSV export on Management+; full public API on Enterprise. Your data stays yours.
  • Security posture documented. Encryption, subprocessors, retention — all at /trust.
  • Hawaiʻi-first roadmap. Feature priorities come from real Hawaiʻi STR owners. I'm not building for Airbnb hosts in Nashville. If a county ordinance changes Tuesday, the rule engine updates Wednesday.
06 — Get in touch

Questions, edges, ordinances I missed.

07 — Begin

Stop losing weekends to filings.