These upgrades can absolutely boost views and bookings, and they can also create a sizable tax deduction.If you have any examples to share, feel free to leave a comment so our community can draw inspiration from your experiences!

For example, mountain markets usually have lower land value, but beachfront is usually higher.

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.

And when they aren’t stress-tested early, they become fragile.One of the clearest examples is inspections.

If an LLC is owned by two partners, for example a family member and myself, and the LLC takes on a DSCR loan with no personal guarantee from the partner in Chapter 13, has court approval typically been required in your experience?

For example, I understand a prospective buyer would want the address, but we are hesitant to put that out public in a listing, as we don't want the home owner to have people trying to go see the house.3) How and when do we talk to the homeowner about the fact we may be selling the note?

The one thing I would add is to run the actual turnover math before deciding how aggressive to go, because the cost of getting it wrong is higher than most people realize.Here is a real example from our properties in Dorchester.

Each handoff is an opportunity for assumptions to break.Rent expectations are a common example.

In markets that have vacancy decontrol (New York's previous system, for example), landlords can reset to market rate when a tenant moves out.

When you sell, they recapture that benefit by taxing you on the depreciation you took.Let me run through a simple example to make this concrete.Say you bought a rental property for $100,000.