Prepared for Kim · Strategic Profits

A simple operating system for your day-to-day

One board holds everything — your requests, your Airbnb guests, house checks, and card activity — and Winnsi keeps it running. Here’s the proposed setup, a short list of questions, and an easy way to answer them from your own Claude Code.

A 5-minute read · then a few questions at the bottom
01 / THE SYSTEM

How it works, at a glance

Requests from Kim Airbnb guests House inspections Bank & card activity Amber = you & Winnsi’s daily rhythm Runs on the Mac mini
Kim's operating system architecture Four feeders send cards into one Trello board. An always-on Mac mini runs the automated jobs. Kim requests and approves; Winnsi operates the board and sends daily digests. asks digest runs digest runs Requests from Kim Anything she needs → a card Airbnb guests Answered 24/7 · escalates to a card House inspections Local walk-through → report + flags Bank & card activity Daily summary · asks only if needed Always-on Mac mini Runs the automated jobs, quietly THE ONE BOARD Trello Inbox · Today · Doing Waiting · Done Everything lives here Principal Kim Requests · approves · reads digest Assistant Winnsi Runs the board · AM + EOD digest

One board

Everything becomes a card in one place — nothing gets lost in scattered texts or WhatsApp.

Four feeders

Your requests, Airbnb messages, house checks, and daily card activity flow onto the board automatically.

Always-on Mac mini

A small computer runs the automatic parts quietly in the background, 24 hours a day.

You & Winnsi

You ask and approve. Winnsi runs the board and sends you a morning digest and an end-of-day recap.

02 / THE AIRBNB PIECE

Answering guests after hours

For guest messages when Winnsi isn’t working, we recommend a service called Hospitable (about $29–44/month). Here’s the short version.

What it gives you

  • Answers guests 24/7 in your own words, using your house info
  • Official Airbnb partner — replies right inside the Airbnb inbox, reliably
  • Anything it’s unsure about is handed to Winnsi instead of guessed
  • Turns real guest issues into a card on the board automatically
  • Priced for a single rental — no big-portfolio contract

When you might want something else

  • Enso Connect — if you later want deeper custom rules and will pay more
  • HostBuddy (~$7/mo) — only if you adopt a full property-management tool
  • A full management platform (Guesty / Hostaway) — only if the rental grows into several listings
Bottom line: Hospitable is the right place to start — lowest cost, answers in your voice, hands off to Winnsi when needed, and feeds the board. We’d only revisit it if the rental scales up.
03 / A FEW QUESTIONS

What we need from you

These shape how we build it. Don’t worry about getting them perfect — the tool at the bottom will walk you through them.

Access & roles

  1. What should Winnsi be able to do on her own, and what needs your sign-off? (e.g. reply to guests herself vs. draft-only; never move money; you approve charges)
  2. Which accounts should Winnsi log into directly (Airbnb, email, Trello, bank/card), vs. use without seeing your passwords?
  3. Who should get the daily finance summary and approval questions — you, Winnsi, or both?

Task tracking

  1. Do you use one Trello board for everything today, or several?
  2. How do you prefer to hand off a request — text, email, or voice memo?
  3. Do you want a morning digest + end-of-day recap from Winnsi each day?

Bank & card

  1. Do you use an Apple Card? And what other cards/accounts should be tracked?
  2. Is the goal business-vs-personal sorting, spending visibility, or both?
  3. Any dollar amount above which you want to be alerted about a charge?

Airbnb

  1. Are you open to using Hospitable (~$29–44/mo) to answer guests after hours?
  2. What are the top ~10 questions guests ask after hours?
  3. What kinds of messages must always go to a person instead of an auto-reply?

House & setup

  1. Do you already have a local person for on-site checks, or do we need to find one?
  2. Can you share your current Google inspection checklist?
  3. The system runs on a spare Mac mini our team sets up — any concerns?
04 / THE EASY WAY TO ANSWER

Let your Claude Code interview you

Instead of typing out answers, paste the prompt below into your Claude Code. It will ask you one question at a time, then hand you a clean summary to send back to Ben.

STEP 1

Open Claude Code on your computer.

STEP 2

Copy the prompt and paste it in. Answer the questions as they come.

STEP 3

Copy the summary it gives you and text or email it to Ben.

You're helping me (Kim) answer a short intake questionnaire for a new personal operating system my team is setting up for me. Please interview me conversationally: ask ONE question at a time, wait for my answer, keep it friendly and plain-language, and never overwhelm me with a wall of questions. If a question has an obvious sensible default and I'm unsure, suggest it and move on.

Walk me through these, in order:

ACCESS & ROLES
1. What should my assistant Winnsi be able to do on her own, vs. what needs my sign-off? (e.g. reply to Airbnb guests herself or draft-only; never move money; I approve charges)
2. Which accounts should Winnsi log into directly (Airbnb, email, Trello, bank/card), vs. operate without seeing my passwords?
3. Who should get the daily finance summary and any approval questions — me, Winnsi, or both?

TASK TRACKING
4. Do we already use one Trello board for everything, or several?
5. How do I prefer to hand off a request — text, email, or voice memo?
6. Do I want a morning digest and an end-of-day recap from Winnsi each day?

BANK & CARD
7. Do I use an Apple Card? (yes/no) What other cards or accounts should be tracked?
8. Is the goal business-vs-personal sorting, spending visibility, or both?
9. Any dollar amount above which I want to be alerted about a charge?

AIRBNB
10. Am I open to using Hospitable (about $29–44/mo) to auto-answer guests after hours?
11. What are the top ~10 questions guests ask after hours?
12. What kinds of guest messages must always go to a person instead of an auto-reply?

HOUSE & SETUP
13. Do I already have a local person for on-site inspections, or do we need to find one?
14. I can share our current Google inspection checklist separately — just note that.
15. The system will run on a spare Mac mini our team sets up — any concerns?

When we've gone through all of them, compile my answers into a clean, organized summary under the same headings, so I can copy it and send it to Ben. Start now with question 1.