Mountain ski places, lakefront etc.I could never bring myself to pull the trigger.

A professional manager does not eliminate the tasks, they just have a system that handles the uneven load.I have not pulled the trigger on hiring a PM yet, mostly because my vendors are good and my tenant base is stable.

The valley's gotten competitive, and a lot of the easy deals have dried up.

It's not a simple as one fits all.Stay liquid enough to be a rare source of funds in dry times.

After that I stretch it out more, maybe every 10-14 days for the next few touches.But I also layer in trigger-based touches.

After the ADU we got a new heloc on the property to have dry powder for future investments and to consolidate various forms of debt we used to build ADU.  

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.

My understanding is that people who try to get REPS and do this with LTR have a lot more IRS pushback, whereas in STR with the STR Tax Loophole (hope I don't trigger the 'but ackshually' guy again), it is easier.

Before focusing only on occupancy, make sure the structure is compliant with local zoning, boarding house regulations, fire code, and short-term rental rules in Syracuse — mixed-use (Airbnb + long-term) in one building can trigger different classifications.On strategy:Running 100% Airbnb in a shared-bath layout can be tough seasonally in upstate NY unless you’re near a strong demand driver (hospital, university, event venue).

What would you want to know before pulling the trigger on a deal like this?