For Eric · P3 Miami · prepared 2026-05-12 · audience: you, considering hardware spend to get tools running 24/7
TL;DR
The cheapest real fix is a dedicated Mac mini at the office, on Tailscale, set to never sleep. ~$600 one-time, no monthly recurring beyond Tailscale free tier. Keeps every connector you have today working (including iMessage, BusyCal, AppleScript) and lets your laptop and iPhone keep talking to it from anywhere.
Your home golf-sim PC is technically eligible (Cowork supports Windows now), but switching to it would silently break ~half your connectors — iMessage, BusyCal, Apple Notes, AppleScript, and any Mac-shell automation are macOS-only. Detailed table inside.
The bigger win is moving as much work as possible OFF any device. Most of your GAW pipeline (scrapers, agenda breakdowns, lobbyist watch, evening digest, freshness monitor) already runs on GitHub Actions in the cloud — those don't care if your laptop is closed. The two-window email cadence (6 AM / 9 PM ET) fires from GitHub Actions, not your Mac.
Your direct question, answered
"Can I run this on my PC and use my Mac and iPhone to run queries on the data?"
Mostly no — and the asymmetry matters. Each Cowork instance runs locally on the device it's installed on. There is no "server" architecture where one machine serves Cowork to others on the LAN. Your iPhone Claude app and Mac Claude app each have their own Cowork session if/when you start one. What does sync across devices: chat history (Pro/Max can message Claude from phone and have a task continue on the desktop, as long as the desktop is awake and Cowork is open). What does not sync: connectors, scheduled tasks, file system access, MCP authentications. Each device authenticates its own Gmail/Box/Notion/etc.
So if you run Cowork on the PC, you'd have to re-auth every connector there, lose all your macOS-only connectors (iMessage, BusyCal, AppleScript), and your Mac and iPhone wouldn't query the PC — they'd run their own Cowork sessions or skip Cowork entirely. The PC's value would only be that its scheduled tasks run 24/7. Which is exactly the value of a Mac mini in the same setup, but without the connector loss.
Option A — Dedicated Mac mini at office (RECOMMENDED)
Every connector you have today keeps working — including iMessage, BusyCal, Apple Notes, Spotify AppleScript, Control_your_Mac.
Hardware is ~$600. You'd add a $25 HDMI dummy plug so it doesn't refuse to wake without a monitor.
Tailscale free tier lets you reach it from your MacBook / iPhone with no port forwarding, no firewall rules, no router config.
Move your scheduled tasks (inbox-refresh, busycal-sync, future overnight CAO sweeps) to it. They fire even when your laptop is in Coral Gables.
Same Apple ID = iMessage works, Apple Notes work, you sign in once.
Cons
Up-front purchase. Counts against your normal Cowork usage allocation (the Mac mini is "another active Cowork member" if you're billing solo, but you're on the same plan, so it's the same bucket).
Physical thing to keep alive — power outage, AC failure, internet drop = it stops.
Cowork usage adds up. With scheduled tasks running 4x/day on top of your laptop usage, watch your monthly cap.
Connector
Works on this option?
Note
iMessage
YES
Reads ~/Library/Messages/chat.db; Mac-only
BusyCal
YES
BusyCal is a Mac app
Apple Notes
YES
AppleScript bridge
Macos__Shell / osascript
YES
The core "let Claude drive your Mac" tool
Gmail / Calendar (Google)
YES
Cross-platform — works on either OS
Dropbox / Box / OneDrive sync
YES
Files arrive automatically
Option B — Repurpose home golf-sim PC for Cowork
Hardware: $0 (already own) · Software: $0 · But hidden cost: ~half your current connectors break
Not recommended for your stack
graph LR
PC["Golf-sim PC @ home Windows 11 + Cowork Hyper-V VM required"]
Cloud["GitHub Actions + Cloudflare Worker"]
Anthropic["Anthropic API"]
Laptop["MacBook"]
iPhone["iPhone"]
Anthropic --- PC
Anthropic --- Laptop
Anthropic --- iPhone
Cloud --- PC
Cloud --- Laptop
PC -.broken connectors.-> X1["iMessage ❌ BusyCal ❌ Apple Notes ❌ AppleScript ❌"]
Pros
Free — you already own it and it's already on.
Cowork DOES run on Windows now (Hyper-V VM, Windows 10/11). Anthropic released this earlier this year.
Could host the GAW data layer if you ever moved off Cloudflare Worker (you wouldn't — Cloudflare is fine).
Cons (the real story)
iMessage on this PC = impossible. The MCP reads the Mac chat.db; Windows has no equivalent.
BusyCal on this PC = impossible. BusyCal is Mac-only software.
Apple Notes, AppleScript-based Spotify, Control_your_Mac on PC = impossible. AppleScript only exists on macOS.
Macos__Shell (the most-used connector in your stack) = impossible. Same reason.
You'd be running two Cowork instances (PC + MacBook) which doubles your Cowork compute usage AND doubles re-auth churn for connectors that DO work on both.
Your iPhone and MacBook can't "query the PC" — they'd still be making their own Anthropic API calls, just with their own connector authentications.
Connector
Works on this option?
Note
iMessage
NO
Mac-only
BusyCal
NO
BusyCal is Mac-only
Apple Notes
NO
macOS app
Macos__Shell / osascript
NO
AppleScript is macOS-only
Gmail / Calendar (Google)
YES
Cross-platform
Dropbox / Box / OneDrive sync
YES
Works on Windows
Govt Agenda Watch MCP
YES
Lives on Cloudflare; OS-independent
Option C — NAS / Synology / Unraid for file sync + always-on Mac for Cowork
Hardware: $400-800 (Synology DS224+ ≈ $400 empty / $600 w/ 2x 8TB) + Mac mini ($599) · ~$1000-1400 total
Single source of truth for files. No more "which version of this is canonical."
Snapshot backups protect against ransomware / accidental deletion (your current Dropbox does some of this).
NAS can also host Docker containers — you could run your own caching layer, photo storage, video transcription, whatever.
Bonus: Plex / TimeMachine targets if you care.
Cons
Solves a file problem you don't actually have. Dropbox already syncs your files everywhere. Adding a NAS for sync is a redundant layer.
Two devices to manage instead of one.
Cowork doesn't run on the NAS itself (no macOS / Windows). The NAS is just a file server.
Total cost ~2x of Option A for marginal benefit on the workflow side.
Option D — Hybrid: Mac mini for Cowork + Synology for backup/sync
~$1000-1400 total · "I want belt + suspenders"
Worth it only if backup peace-of-mind matters separately
Pros
All upside of Option A + dedicated backup that lives in your office.
If you ever leave Dropbox (cost / policy reasons), you've got the infrastructure.
Synology can hold your CAO opinion archive locally if Dropbox rate-limits or syncs slowly.
Cons
More upfront cost. More things to maintain.
You're already on Dropbox Business — there's no acute backup gap to solve.
Option E — Status quo (laptop only), but move every scheduled task to GitHub Actions
$0 hardware · ~4-6 hours of my time to rewrite tasks
Free workaround — won't fully solve, but covers most pain
Pros
$0. Best ROI on a "before-you-buy-anything" basis.
The morning + evening digests, GAW scrapers, agenda breakdowns, freshness monitor, lobbyist watch are ALL already on GitHub Actions today — they don't need your laptop.
Remaining laptop-dependent items: inbox-refresh (Gmail pull via Cowork), busycal-sync, anything that needs Macos__Shell. Most of these can be rewritten to run on GitHub Actions:
Inbox refresh → Gmail API via GitHub Actions (no Cowork needed)
BusyCal sync → keep on Mac (it must run on macOS to write to BusyCal anyway)
CAO opinion ingest → already on GitHub Actions
Cons
Doesn't solve iMessage / BusyCal / AppleScript work — those still need a Mac that's awake.
Doesn't help when you're at a hotel and want to pull Gmail RIGHT NOW with Cowork — your laptop has to be on.
You'd want this AND Option A long-term anyway. Doing it now narrows the gap.
Recommendation matrix
Option
Up-front cost
Complexity
Mac connectors preserved?
iPhone access?
Solves "always-on"?
A. Mac mini at office
~$600
Low (1 device + Tailscale)
YES (all)
YES (Tailscale)
YES
B. Golf-sim PC (Windows)
$0
Medium (re-auth all)
NO (iMessage / BusyCal / AppleScript break)
Partial
YES, with caveats
C. NAS only
~$400-600
Medium
n/a (NAS doesn't run Cowork)
Files yes, Cowork no
NO (Cowork still needs a host)
D. NAS + Mac mini
~$1000-1400
Medium-high
YES
YES
YES + backup
E. Status quo + move tasks to cloud
$0
Engineering time only
Existing Mac connectors keep working
Partial
Partial (cloud parts only)
If I were spending your money
Do Option E first (free, takes me a few hours overnight to migrate inbox-refresh + a few other scheduled tasks to GitHub Actions). Then if you still feel the pain after 1-2 weeks, add Option A — buy a Mac mini, drop it at the office, set Caffeine, install Tailscale, install Cowork, sign in, re-auth Gmail / Box / Dropbox / GAW. Total cost ~$600 and you stop ever caring whether your laptop is closed.
The golf-sim PC stays on the golf sim. Cowork on Windows is real, but your stack is too Mac-centric for it to help you.