New thing, starting in two weeks. Coffee Chats are one live hour, twice this month, then monthly. Tuesday September 15 at 12pm Toronto time. Bring one thing you are stuck on and leave with a decision instead of a list of options. Open to everyone. You do not need to be a paid member to be in the room. The replay is the part that lives in Premium. That is the honest split: the conversation is open, the recording is what a membership holds. Post your question in the community beforehand if you want it answered first. I would rather walk in with three real problems than a slide deck. What would you bring?

Most hosts check things remotely that a person standing in the property could answer in four seconds. Is the parking spot clear. Did the last guest leave the patio furniture out. Is the coffee running low. Did the shower drain slow down again. Your cleaner is already there. They are already looking. The only reason they do not tell you is that nobody asked them to. I am not suggesting more work for them. I am suggesting three questions attached to a job they already do. What is the thing you check most often that someone else could check instead?

Ten minutes today. That is the whole ask. Pick one piece of information about your property that exists nowhere except your head. Where the water shutoff is. Which burner runs hot. That the second parking spot is technically the neighbour's after 6pm. The wifi password that is not on the fridge. Write it somewhere a stranger could find it. That is it. Not a system, not a binder, one sentence in a document. The reason this matters: every one of those undocumented facts is a moment where someone has to reach you. Ten of them is ten interruptions a month. What did you write down? Post it, and someone else will realize they have the same gap.

Every task in your operation lands in one of three piles. Built once, runs alone. The check-in message, the house manual, the cleaner's checklist. You made it, it works without you. Still yours. The things that genuinely need your judgment. Pricing calls, a difficult guest, whether to take the booking. Neither. The tasks you do manually every single time that could have been built once, and never were. This is the pile that eats your evenings. Pick five things you did for your property in the last two weeks. Sort them. Post your third pile below. That list is your actual to-do list, and it is usually shorter than people expect.

I've been in real estate investing for almost 10 years now and I'm mainly here to learn from people actually doing this day to day. I don't have an STR live yet, still in the planning stage for a property, so my biggest challenge right now is figuring out how to systemize guest communication and turnovers before I ever list. I also run a small software company, but that's not why I joined, just want to learn, add value where I can, and get to know some of you. Feel free to say hi.