Just a heads up.

January tends to pick up, so if you can get ahead with marketing and photos, you’ll be in better shape.When you start screening tenants, pay close attention to any prior rental-related debts, open collections, or bankruptcies...those are some of the biggest red flags you can catch early.For leasing, get your listing on as many platforms as possible (not just Zillow), and respond fast to every inquiry.

You’re already ahead by owning and renting out two properties.

However, a caveat is that we will accrue these losses across the entire year; they don't exist yet.My understanding is that IRS safe harbor laws could allow us to simply pay 110% of 2025 taxes (or 90% of 2026 taxes, however this will be hard to predict ahead of time).

At your age I would say go ahead and try it out. 

It's great that you're an alum, you've got a head start on understanding the market and a tenant's perspective.I've been a student housing specialist in Binghamton for almost ten years and have seen a lot of changes over that time.

Also, and I am guilty of this, don’t tell them ahead of time what the other service company said because then it’s sort of like leading the witness and it encourages them to come up with the same diagnosis.

Should I involve an attorney ahead of time to check for liens, back taxes, or other encumbrances that might transfer with the property?

Most investors look at their numbers once a year — usually when their CPA asks for them in March.By then, it’s too late to make changes.The best investors I’ve worked with — the ones who always seem one step ahead — have a habit I call the Quarterly Check-In.Every 3 months, they:- Review income and expenses for each property.- Check if their financing or insurance still makes sense.- Plan upcoming repairs or improvements before they become emergencies.- Look at their tax position and make small moves early — instead of big ones in a panic later.It doesn’t take long.

Sean — great question and glad you’re thinking ahead before tax season ramps up.I’m a CPA who works almost exclusively with real estate investors, agents, and short- and long-term rental owners.