Source file
/Users/josephbowens/Desktop/SkyRun/Homeowner Onboarding Checklist (1).xlsx
Sheets:
- Winter Park Properties 2025 — last year's onboardings (reference)
- Winter Park Properties 2026 — current year (active)
- Vermont Properties — VT is on hold, but checklist template exists
- Amenities Checklist — per-property required amenities
The 14 canonical tasks (per property)
Every new property runs through this list after the Management Agreement is signed:
| # | Task | Owner |
|---|---|---|
| 1 | Owner Agreement Signed | Rachel |
| 2 | W-9 | Brooke |
| 3 | Owner Questionnaire Sent | Rachel |
| 4 | Wifi Set Up | Brooke |
| 5 | Signage and SkyRun items set up | Brooke |
| 6 | Photos | Brooke (sometimes Mandy) |
| 7 | New Lock Installed + Maintenance walkthrough | Byrne |
| 8 | STR license and Copy of Homeowner Insurance + "additionally insured" endorsement | Mandy |
| 9 | Deep clean completed and billed | Mandy |
| 10 | Linens dropped for Deep Clean | Brooke |
| 11 | Hot Tub Company notifications set up | Mandy |
| 12 | Blue Bag and Tag | Brooke |
| 13 | Tracks Profile / Airbnb Fields | Mandy |
| 14 | Operto | Brooke |
Complete / In Progress / Not Yet Started
How this pairs with our BD system
- Signing trigger — when a deal moves to "Signed" in HubSpot, create a new property row in this checklist
- Tracking — the checklist IS the handoff doc from BD (Joseph) to Ops (Rachel, Mandy, Brooke, Byrne)
- STR + Insurance + additionally insured — item 8 is the insurance objection-killer. Grand Lake insurance is especially relevant (see
reference_grand_lake_risk.md). Rental Guardian ($50/res, $25K contents + personal liability) is the in-house answer if owner can't get their own rider. - Active roster — once items 1 + 13 are done (agreement signed + Track profile created), the owner should appear in the next Rachel-provided active-homeowner list export
How to apply
- When asked "where are we with [property] onboarding?", check this file
- When drafting deliverables, item 8 (insurance-additionally-insured) is worth surfacing as a pain-killer
- When discussing BD-to-Ops handoff, reference this as the authoritative list
- The W-9, insurance, deep clean, and Track profile gate the owner's first payout — delays here delay revenue
Related
reference_active_homeowner_roster.md— the output of completed onboardingsreference_ops_stack.md— Operto/Track/etc. referenced in the checklistreference_owner_agreement.md— the upstream signed agreementreference_grand_lake_risk.md— Rental Guardian context for item 8