Maui Kaanapali Villas · August 2026 A proposal to work together differently
Chief AI Officer
Partnership

One partner, for a fixed term, who builds the association a single place to look, numbers of its own, and one way to reach every guest and every owner.

Prepared by LONELY PINE AI
For Hal, Chief Executive, AOAO of Maui Kaanapali Villas
Where this starts

A 302-unit resort,
without a single place to look.


The information the association needs is real, and the team collecting it is doing the work. It just lives in different systems, different spreadsheets, different inboxes, and in a few cases in the mail.

So when the rental operator's corporate report disagrees with what the front desk is seeing, there is no third source to settle it. When the rental committee says the property slipped, MKV answers for a number it did not produce.

None of that is a failure of effort. It is a missing layer. This proposal builds that layer.

The status quo

What the association absorbs today


Numbers that do not reconcile

Operator corporate reporting and on-site front desk reporting disagree, and MKV has no independent figure to bring to the conversation.

Systems that are worked around

The association pays for platforms the team works around rather than through, and nobody can point at what either one returns.

Commercial rent moving on paper

Check, envelope, post, management company, receivables, deposit. The percentage-of-gross calculation is also done by hand, when it is done at all.

Guest issues routed to the AOAO

Pest control is an association contract, so complaints against rental-program units land on MKV to service and to answer for.

Where this comes from

Most of this is already built.
The work is adapting it to MKV.


These systems run today for other Hawaii properties. MKV would be adopting proven software and having it fitted to the association, rather than paying to invent it.

A command center

Role-scoped operating picture with an assistant that answers from the organisation's own documents and moves the screen to the answer.

Guest communications

Automated arrival-to-departure guest sequence with staff-editable content, surveys, and property broadcast. Running at a Kaanapali resort a few properties from MKV.

An owner and reservations console

Document intake, review before anything publishes, and owner records for a Kihei resort association.

The role

What Chief AI Officer actually means


01.

Strategic direction

Lonely Pine takes the technology relationship off the association's desk. Evaluating what MKV pays for, retiring what does not earn its keep, and standing between the association and the next vendor pitch.

02.

The build queue

Continuous delivery against a rolling priority list, re-ranked monthly. No per-feature change orders. Something usable ships every two weeks.

03.

Operating what is live

Once a system is running it is ours to keep running. Bug fixes, seasonal tuning, policy changes, new staff. No change orders for the board to approve.

Not included: board approvals and governance, the rental operator's own systems and staffing, hardware and cabling, and anything that is not software, automation, or AI.

Phase 1

The Command Center


One place to look, scoped by role. Hal and the on-site lead see the whole property. Each department head sees only what their role requires.

Ask

A question in plain language against MKV's own documents, contracts, minutes, and standard procedures. The answer arrives with its sources, and the screen moves itself to the relevant view.

Invoice intake

Upload an invoice as a photo or a PDF. It is read automatically, uncertain fields are flagged for a human, and nothing posts until a person approves it.

Commercial tenant billing

The spa lease calculated every month without anyone doing the arithmetic: the $1,500 base against 8 percent of reported gross, whichever is greater, invoiced and tracked to payment.

Documents and department map

Every association document searchable and permissioned. Systems and responsibilities as a connected chart, named by department rather than by person.

Phase 1 · What it looks like

The Command Center


mkv.command · signed in as Hal
MAUI KAANAPALI
VILLAS
Command
Ask
Documents
Invoices
Commercial tenants
Departments
Reports
Property overview Executive view
214
On property
17
Open work orders
4
Invoices to review
4.3
Guest rating

Maintenance

17 open, 5 older than 72 hours. Two are pest control in rental-program units.

Recommend: close the two pest items before the operator's next report.

Commercial tenants

Spa gross reported at $24,800. 8 percent exceeds the base rent this month.

Recommend: invoice $1,984, not $1,500. Ready to send.
Ask · "What did we agree with the spa on percentage rent?"
The lease sets rent at the greater of $1,500 base or 8 percent of monthly gross sales, reported by the 10th.
Source: Commercial lease, section 4.2 · opening Commercial tenants

Indicative layout in a cream and green palette, pending the association's brand assets.

Phase 2

Guest relations, owner communications,
and numbers of MKV's own


Capture

Arrivals and census

Staff entry at the desk or guest self-service by QR code. Vehicle plate for parking, party size, unit.

Sequence

Automated guest journey

Welcome, mid-stay check-in, activities, and post-stay survey. Each on its own schedule, each with a manual override.

Reach

Broadcast to guests and owners

Property-wide, by category, or to specific units. Room status, property updates, activities, safety and weather.

Report

MKV's own monthly report

Built from data the association enters and controls, so MKV finally holds a number of its own.

The front desk edits tours and pricing directly, with no developer and no ticket. Phase 2 runs entirely on MKV's own data entry, so it works without waiting on anyone else's cooperation.

Phase 2 · What it looks like

Guest and owner communications


mkv.guests · front desk
Guests Messages Activities Surveys Broadcast Audit
214
On property
31
Arrived today
27
Departing today
4.3
Survey average
UnitGuestPartyPlateSequence
A-418Nakamura4HGT 442 WMAS
B-247Whitfield2KLM 118 WMAS
C-105Alvarez6PRT 903 WMAS
Broadcast
All owners All guests on property Specific units Pool closure Weather advisory Emergency

W, M, A, S are the welcome, mid-stay, activities, and survey messages. Filled means sent.

Phase 3

The field app


For maintenance, security, and grounds. Web-based, so it installs from a link. No app store, no IT rollout, no new hardware.

Work orders

Dispatched to the crew and accepted in the field, with job history attached to the unit and the property record.

Incident reports with photos

Timestamped, filed against the property record, and retrievable later when someone asks what happened and when.

Crew performance ratings

Earned from completion, timeliness, and quality, so the right crew is matched to the right job.

Phase 3 · What it looks like

In the crew's hand


MKV Field
Grounds · Manny
WO-1184 · Today
Beachwalk tree trim
Section C, start at the north end
AcceptDetails
WO-1179 · In progress
Pool deck lighting
2 of 5 fixtures replaced
WO-1166 · Complete
Lobby door closer
Incident report
Security · overnight
PHOTO ATTACHED
PHOTO ATTACHED
Logged 02:14 · Building B
Broken gate latch
Pool gate will not latch. Secured with temporary chain, maintenance notified.
SubmitAdd photo
My rating
This month
Current tier
A · 4.6
On time
94%
Completed in window
88%
Jobs closed
31

Indicative screens. Higher-rated crews are matched to the jobs that need them.

Security and what MKV keeps

Your accounts. Your code. Week one.


MKV keeps everything

Code, data, domains, and credentials in the association's name from the first week. No holdback, no exit fee.

Sign in with Google

The Workspace accounts MKV already uses. Access is enforced before a request reaches the application, and a valid login alone is not enough. A person must also be on the roster for their role.

Audited infrastructure

Runs on Cloudflare with Anthropic providing the language model. Both are SOC 2 Type II certified. Lonely Pine is not itself a SOC 2 audited entity and does not claim to be.

Full audit trail

Every send, edit, approval, and login recorded and reviewable. Infrastructure billed to MKV at cost with no markup.

The investment

Fixed term. Defined end. No build fee.


These are engagements with a finish line, not an open-ended retainer. The monthly is shown for budgeting. The total is what the board is approving.

Foundation · 3 months

$19,500 total

$6,500 per month
  • Phase 1, the command center
  • Phases 2 and 3 quoted separately later
Partnership · 4 months · Recommended

$32,000 total

$8,000 per month
  • Phases 1 and 2
  • Guest and owner communications
  • MKV's own monthly reporting
Acceleration · 3 months

$56,250 total

$18,750 per month
  • All three phases
  • Field app included
  • Complete by December 31, 2026

Acceleration is the better buy if the board can move. Adding the field app later as its own project would be quoted at $25,000 to $30,000, putting Partnership plus that purchase at $57,000 to $62,000 and finishing well into 2027. Acceleration delivers the same scope for $56,250, done by December 31. It requires a start no later than October 1.

What this actually costs

The command center, guest and owner
communications, and your own reporting.

$105.96 / unit
Partnership · 302 units · one time

Not per year. That is the whole four-month engagement, divided across the units that pay for it. $26.49 per unit per month while the work is running, and then it stops.

Foundation

$64.57 per unit
$21.52 per unit per month

Partnership

$105.96 per unit
$26.49 per unit per month

Acceleration

$186.26 per unit
$62.09 per unit per month

After the build, and the terms

When the engagement ends,
the spending drops.


There is no rolling build fee. The system moves to operate and improve at $1,500 to $2,000 per month, under $7 per unit, covering infrastructure billed at cost plus monitoring, support, seasonal tuning, and small enhancements. MKV can also decline it, take the system, and run it in-house. The accounts are already in the association's name.

Fixed term, no auto-renewal

A defined end date. At the end MKV either moves to the operate rate or takes the system and walks.

30 days notice to exit early

Either side, with the final month pro-rated.

Source code in MKV's repository

From week one. Never held back as leverage. No non-solicit.

Invoiced on the 1st, Net 7

Card or ACH. Infrastructure passed through at cost with no markup.

The ask

What I am asking for


Not a signature. A yes or no on the model.

If yes

  1. MKV picks an engagement. Recommended: Partnership, four months, $32,000 total.
  2. I run a live walkthrough for Hal and anyone the board wants in the room, using the systems already running at other properties. Not slides.
  3. I draft a short engagement letter, not a long statement of work, within 48 hours of the decision.
  4. Work begins the 1st of the month following board approval.

If the board wants all three phases finished this calendar year, the decision needs to land in time for an October 1 start. I am on Maui from August 30 through September 9 and would rather do this part in person.