If you do it, require written disclosed dual agency, define exactly what the agent can and cannot advise on, and add protections: independent inspection, your own appraisal/comps, and an attorney or transaction coordinator on your side.

Once they get established, they tend to spread between units through walls, outlets, and plumbing chases.I’d recommend a coordinated treatment plan for the whole building rather than trying to pinpoint one tenant as the source.

Take Advantage of Active Income Treatment (the “STR Loophole”)Here’s the big one:If you materially participate in managing your short-term rental — handling bookings, messaging guests, cleaning coordination, and pricing — your Airbnb income may be treated as active, not passive.Why that matters: Active income allows you to use losses (like depreciation or upgrades) to offset your other active income — even W-2 income in some cases.

That timing also gives you the rest of the month to properly introduce yourself to the tenants as the new landlord and coordinate how rent will be paid for the following month.

I coordinated 40+ deals for people, a deal that looks good on paper does not mean it will translate to real world results. 

Excellent points — both of you are spot-on.True mezzanine financing only works when the senior lender understands and accepts the intercreditor structure, and that coordination is usually where deals stall.At Modern Financial, we’ve seen that complexity firsthand.

I can't imagine anyone knowingly let that switch happen, which makes me think that a bunch of professional hosts were asleep at the wheel and didn't opt out.These are all properties with 6+ bedrooms and the typical guest profile is a multi-family or multi-gen group booking far in advance -- 6-12 months out, because they are coordinating availability across a bunch of people.

Learned a lot about the process while property is under contract (coordinating home inspections, appraisals, getting documentation to the lender, etc) I should have locked in my interest rate two weeks ago before they shot up recently!

Keep logs of your time spent on bookings, cleaning coordination, and maintenance.If you do that, yes, converting a small boutique hotel into STR units can be a powerful tax play with big upfront write-offs.

But numbers on a screen don’t replace:Negotiation leverage – A seasoned agent knows how to structure terms, not just price, to win deals.Boots on the ground – Someone has to physically verify property condition, meet inspectors, and ensure you’re not inheriting hidden problems.Local market insight – Zillow comps are not always accurate.Transaction management – Coordinating title, contractors, appraisers, tenants, and property managers takes systems and experience.For out-of-state investors, paying an agent’s fee isn’t just about MLS access, it’s about protecting your investment, avoiding costly mistakes, and maximizing ROI.