in 2024 completed a 2 story detached ADU which includes a fully insulated large 2 car garage/shop with half bath, and a custom 2 bed/1ba apartment above (not builder grade, pretty fancy).  

We tested Monday and ended up building our ops around ClickUp as the system of record, with our PMS and automations feeding it.How we run STR ops (high level)PMS drives the truth (reservations, changes, cancellations).Automation pushes events into ClickUp so humans work from tasks, not inboxes.For example: Guesty → webhook → database layer → create/update ClickUp tasks for inquiries + reservations, with custom fields like check-in/out, guest, listing, status, conversation links, etcWe also automate “edge-case ops” like pool heat, early check-in, late checkout, pets, extra guests by generating subtasks/checklists off a request.Where Monday tends to feel greatFast to set up boards, very visual.Good for simple pipelines: turns, maintenance queues, onboarding checklists.Dashboards and “who owns what” is easy for teams that hate complexity.The biggest hurdles / limitations people hit with Monday in STR (in my experience)When the PMS needs to be the source of truthSTR is event-driven: reservation updates, cancellations, date changes, channel messages.If Monday is the “truth”, you end up reconciling drift constantly.Automation ceilingMonday automations are solid for basic triggers, but once you want “if X then create Y tasks, keep them in sync, dedupe, move between pipelines, update 15 fields, attach links”, you start wanting a real workflow engine + database.Data model constraintsSTR ops has “objects”: Reservation, Property, Guest, Work Order, Vendor, Owner, Conversation.Monday is board/item-first, so relationships can get awkward at scale unless you build a lot of glue.High-volume operational noiseHundreds of small updates (date changes, guest count changes, messaging, payments, add-ons) can turn boards into a scroll-fest unless you are very strict about what becomes an item vs a log.If someone is committed to Monday, this is the way I would set it upBoards by function, not by property:Reservations pipeline (pre-arrival, in-house, checkout, post-stay)Turns and housekeepingMaintenance and inspectionsOwner requests and approvalsOne unique ID field per reservation and treat it like a primary key.Use an integration layer (Zapier, Make, n8n, custom) so the PMS updates Monday automatically, not manually.Bottom lineMonday is awesome if your ops are mostly human-driven and you want speed + visibility.

After that, everything is pretty straightforward and automatically generated with 2-3 inputs, and each property takes about 5 minutes.

Hey everyone, Jake Heller here.Quick background: I'm a 3rd generation real estate developer.

But I'm still not sure there's a real market for these... they may just be too niche/customized?

You provide housing.Start by understanding the customer.  

Are you using AI for guest communication or more on the lead generation side?

The chart of accounts doesn't map to Schedule E without heavy customization, and if you have multiple properties you end up with class tracking or location tracking that gets messy fast.

We always accept payment prior to a customer moving in.

Most of my customers are looking for distressed properties with potential for a flip.