Part of SMPLR OSIncluded free

Meet Milo.
The AI layer that runs your HOA in the background.

SMPLR AI is a smart layer sitting over the best frontier models — Claude, GPT, Gemini — with HOA management context baked in. Milo knows your CC&Rs, your ledger, your board's tone, and your residents by name. So while you're at your kid's soccer game, the HOA is still running.

Start free for 30 days See what Milo does
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ClaudeGPTGemini+ SMPLR HOA context
MiloSMPLR AI · Oak Ridge HOA
on
Milo — can you remind me what we agreed about pool fobs in March?
You · 9:14 AM

From the March 18 board minutes:

  • One fob per residence, two for owner-occupied homes with 3+ residents.
  • Replacements $25, charged to the homeowner ledger.
  • Lost fobs deactivated within 24 hours.

Source: Minutes — March 18, 2025 · Motion 3, passed 5–0.

Milo · 9:14 AM
Milo is drafting a reply for Lina Okafor about her fob…
A morning in the life of Milo

While you were at the kids' game.

This is a real activity feed from a Saturday morning at Oak Ridge HOA. Six tasks. Eighty-three minutes. Zero board members at a laptop.

06:14 AM
BroadcastAwaiting board approval
Drafted weekly broadcast

Pool opens Saturday · Memorial BBQ RSVP at 78 · ARC deadline reminder

06:48 AM
EmailSent · 2 escalated to board
Replied to 4 resident emails

Refund question · trash schedule · 2× pool fob inquiries

07:02 AM
DuesPosted to ledger
Ran Q2 dues schedule

$94,820 invoiced across 320 homes · 4 autopay corrections

07:21 AM
ReminderDelivered
Sent invoice reminders

12 owners · friendly tone · 3 with hardship-plan offer

08:09 AM
Resident chatResolved · 1 to ARC
Answered 6 chat questions

Fence color · short-term rentals · guest parking · pet policy

08:34 AM
Every action is logged, signed, and reviewable.You always see what Milo did, what model it used, and which board policy it followed.
What Milo does

Six jobs the board used to do at midnight.

Milo isn't a chatbot bolted onto a sidebar. It's a working teammate trained on HOA operations, with the keys to the parts of SMPLR that matter.

Broadcast notifications

The weekly email writes itself.

Milo reads your last seven days — meetings, votes, work orders, new vendors, weather alerts — and drafts a community broadcast in your board's voice. You review, edit a sentence, hit send. Three minutes, not three hours.

  • Auto-summarizes the past week from SMPLR data
  • Matches your board's existing tone (formal, friendly, plain)
  • Personalizes by home — Birchwood gets the trash note, Maple doesn't
  • Delivers via email, SMS, or the resident app
Weekly broadcast · awaiting approval
Milo
Draft #284 · 6:14 AM
This week in Oak Ridge — Memorial weekend edition
Drafted by Milo
To All Owners · 320 homesChannels Email · SMS · AppSend Today, 5:30 PM

Hi neighbors — three quick things heading into Memorial weekend:

  1. Pool opens Saturday at 10 AM. Fobs were re-coded yesterday. If yours doesn't work, reply here and Aaron will swap it.
  2. BBQ at the pavilion, Saturday 2 PM. We're at 78 RSVPs — we'll have plenty.
  3. ARC deadline for June projects is Sunday at 11:59 PM. Submissions open on the website.
Resident email

A real reply, not "we'll get back to you."

Milo monitors every board inbox. When a resident emails, it drafts a reply that pulls from CC&Rs, ledger history, past minutes, and recent maintenance tickets. Easy questions go out with one click. Hard ones are flagged for the right board member.

  • Reads CC&Rs and rules to answer accurately
  • Cites the document section in every reply
  • Auto-escalates legal, financial, or hostile messages
  • Always shows the draft before it sends — your call
Inbox · 1 reply ready · 1 escalated
Milo
L
Lina Okaforlina@… · to treasurer@oakridge.com · 9:08 AM

Re: April statement question

"Hey — I see a $25 charge on my account from April 14. Is that the new pool fob? I thought we got one free."

Milo drafted a replyconfidence high · 94%

Hi Lina — good catch. The $25 was a replacement fob (your original is still active per our records, last used 04/12). Per the March 18 board minutes, the first fob is free; replacements are $25.

If your original isn't working, reply and I'll have Aaron swap it free of charge.

📎 Source · Minutes — March 18, 2025, Motion 3 · Ledger row 4128
⚑ escalated
Hostile message from 1408 PecanForwarded to the board · summary attached · do not auto-reply
Dues schedules

Dues that run on the first of the month, every month.

Milo runs the quarterly assessment, applies your fee schedule, prorates new owners, handles partial payments, and posts every entry to the ledger correctly. No more "did Karen run the dues this quarter?" two weeks late.

  • Reads your governing docs for fee schedule + late logic
  • Prorates mid-cycle move-ins / move-outs automatically
  • Generates audit-ready journal entries
  • Pauses on anything ambiguous and asks the treasurer
Q2 assessment run · 7:02 AM
Milo
Run #112
$99,200 invoiced · 320 homes
Ledger posted
320homes billed
4autopay fixed
2prorations
1paused for review
1216 Birchwood Ln · ReyesStandard $310 · autopay set for 4/28
Scheduled
1304 Pecan Ln · Chen (new owner)Prorated $186.45 · closed 4/12 · 21 days remaining
Prorated
1820 Oak Ave · OkonkwoPossible double-billing detected — held for treasurer review
Paused
Resident chat — rules & policy

"Can I paint my front door black?"

Residents ask Milo from the SMPLR app, the website, or by SMS. Milo reads the CC&Rs, the ARC rulebook, and the recent architectural decisions, then answers — politely, with citations. If it's a judgment call, it opens an ARC ticket.

  • Cites the exact section of the rules in every answer
  • Knows your last 3 years of ARC precedents
  • Opens a ticket when the answer is "you need to ask the board"
  • Never invents a rule — admits when it doesn't know
Resident chat · rules · live
Milo
D
Diego Rangel1408 Pecan Ln · 8:31 AM

Can I paint my front door matte black? I saw two on the next street over.

Milo · SMPLR AI

Short answer: yes — matte black is on the approved exterior palette (ARC §4.2, "Doors & shutters"). You don't need a separate ARC submission as long as you stay on-palette.

CitedARC Rulebook §4.2 · Approved palette, Rev. 2024
Why HOA context matters

A chatbot is not enough. Milo knows your HOA.

Anyone can wrap an OpenAI key in a UI. What we built is the connective tissue between your governing docs, your money, and your residents — so the AI's answer is the right one for your community.

Situation
Generic AI
Milo (SMPLR AI)
"Can I paint my front door black?"
×

Hallucinates a rule that doesn't exist. Apologizes. Cannot cite anything.

Reads ARC §4.2. Replies with the exact passage. Opens a ticket if unsure.

"Owner is 60 days past due on $620."
×

Drafts a generic dunning letter that sounds like a collections agency.

Writes in your board's voice. Offers the hardship plan you've already approved.

"Run quarterly assessments for 320 homes."
×

Posts dues with no awareness of who's on autopay, prorating, or in dispute.

Runs the full schedule, pauses on anything ambiguous, and asks the treasurer.

"Send out the weekly broadcast."
×

Writes a broadcast that mentions nothing about your actual community.

Pulls last week's tickets, RSVPs, weather alerts, and votes. Personalizes by block.

Pricing

Milo is included.

SMPLR AI ships with every SMPLR OS plan — Community, Multi-Portfolio, every tier. No per-seat fee, no per-message fee, no "AI add-on" upsell on your next renewal. We think AI for HOA management should be like spell-check for email: part of the product, not a feature flag.

Start free for 30 days See plans
Per board seat$0
Per message / per task$0
Model usage pass-through$0
Total monthly add-on$0
Reasonable use policy: Milo runs unmetered for normal HOA workloads. We'll only reach out if a single association generates more than ~10× the volume of a typical community, and even then we'll work it out — not bill you a surprise.
Boards ask us

What does it actually do on a Tuesday?

The honest answers we give every demo, in plain English. If we missed your question, the team is one click away.

Talk to a real human
Does Milo send messages on its own without us approving them?

By default, no. Anything that leaves your HOA — emails, broadcasts, reminders — is drafted by Milo and held for a one-tap approval. You can opt into auto-send per channel once you've watched it work for a couple of weeks. Critical actions like ledger posts, ARC denials, or messages to a flagged hostile owner are always held for review.

Which AI model is Milo, exactly?

Milo isn't one model — it's a routing layer. We use Claude for long-document reasoning, GPT for email and summarization, Gemini for image and logo work, and on-device open-source models for anything we'd rather not send off our servers. The router picks per task and is upgraded as the frontier moves.

What does Milo know about my HOA — and what doesn't it share?

Milo sees only what your board has put into SMPLR: your governing docs, ledger, minutes, vendor list, brand kit, and resident roster. None of that is used to train any underlying model. Calls to frontier APIs go out with zero-retention contracts.

Will residents know they're talking to AI?

Yes — every message Milo sends is signed 'Milo · SMPLR AI on behalf of the board.' The residents we surveyed strongly prefer that transparency. If Milo doesn't know an answer, it says so and opens a ticket instead of bluffing.

Can I turn off specific capabilities?

Every capability is a toggle. A board that only wants Milo to handle invoice reminders can use only that. Settings live under SMPLR AI → Capabilities and changes take effect immediately.

What if Milo gets something wrong?

Every Milo action is logged, signed, and reversible. The audit log shows what was sent, which model drafted it, which document it cited, and who approved it. If a reply turned out to be incorrect, you can issue a one-tap correction.

Start with one community. Or all forty.

Free for thirty days. No card required.

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For management companies with 500+ doors, ask about Multi-Portfolio onboarding.