@Brendan M Hornung If you purchased a subject-to (sub-to) rental property, filing taxes correctly is key to maximizing deductions and staying compliant.

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

I would keep the brokerage account and focus on the tried-and-true practice of saving up for a new investment.

I'd love to hear more to about how we may be able to work together and help our clients maximize their investments.  

.✔️ You want to maximize profits and keep full control.✔️ You’re willing to learn Chicago’s landlord-tenant laws.Consider hiring a property manager if:✔️ You have a busy schedule or don’t want landlord responsibilities.✔️ Your house hack is more than a 2-unit property and requires more oversight.✔️ You’d rather pay for peace of mind and legal compliance.Final ThoughtsIf you’re house hacking a small multi-unit (like a 2- or 3-flat) and are comfortable being hands-on, self-managing can be a great way to save money and learn the business.

Co-living is how I went from renting a room, Delivering Dominos, no savings, and not being able to qualify for a loan to financial freedom & a $2M net worth in 15 months.  

Additionally, cost segregation and bonus depreciation can accelerate tax benefits.Because filing as single taxpayers limits certain deductions, planning in advance ensures you maximize benefits while avoiding complications.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

I could easily see you spending more than you save if you try it with a tiny house. 

Just be sure to research your target markets carefully to maximize returns.