Running an Airbnb or short-term rental can be an incredible cash flow machine — but it can also turn into a tax nightmare if you don’t know the rules.Here’s the good news: the IRS treats short-term rentals differently from traditional long-term rentals — and if you structure things right, you can unlock powerful deductions, reduce taxable income, and keep way more of your profit.So, let’s talk about the Airbnb tax secrets every host should know in 2025.1.

If you like I am happy to meet for a coffee or lunch, chat a little bit? 

Quote from @Jules Aton: Quote from @Paul Sofia: Fink and Co. are all part of the machine. 

You’re building a self-funding machine.

If so, it would be great to meet up for a cup of coffee or something to talk.

Coffee, walking a project, or just talking shop, I’d be grateful for the opportunity.

A couple of things you might try: refreshing your photos or adjusting the listing description to highlight the lifestyle perks of the area (parks, restaurants, coffee shops, etc.).

The demand is usually steady year-round in Chicago for that group.That said, here’s how I’d weigh it:If you go MTR:You’ll need to furnish it properly — not fancy, but turnkey: queen bed in each room, blackout curtains, comfy couch, smart TV, solid Wi-Fi, a stocked kitchen (pots/pans, utensils, coffee maker, toaster), and a simple desk setup.Expect about $4K–$6K upfront to get it guest-ready if you’re starting from scratch.Cleaning and turnover management can be automated (Turno app or a local cleaner), but there’s still some coordination involved.Since you’re near a hospital, list on both Furnished Finder and Airbnb (30+ night stays) — that combo usually keeps you booked.If you go LTR instead:You’ll save yourself the time and mental load of setting up a new system while adjusting to newborn life.Even if the rent’s lower, you’ll get steady income and less stress, which might be worth it right now.Winter leasing in Chicago:Yeah, it’s slower — especially December through February — but MTRs tied to hospitals stay active because medical contracts don’t follow the same seasonality.If this were me?

If you ever feel like trading notes or grabbing a virtual coffee, I’d value the conversation.

it its the machine overflowing its a washer problem .