To House Hack Now or Buy More?

[Sarah Miksa]

Hi! I currently have a large 1/1 with a ton of space in a highly desirable location in Chicago. With interest rates being so high and it being a condo I pay just under 3k/month. The condo surprisingly has no limit on rentals, as confirmed by my lawyer I could Airbnb it if I wanted to. Right now I have a very demanding 9-5 and don’t see running an Airbnb as an option right now. I have a great contractor and have explored adding a bath for 45k and/or add a bedroom (removing the large dining room). If I add a bath I could split the unit and house hack, however I don’t see it covering all of my housing costs/renovation cost at least for some time. Alternatively, if I left the unit as is, or added a bedroom for a much smaller cost by removing the dining room, I could rent the entire unit out on a short or medium term basis, for at or above the monthly cost, then look for a separate house hack with a bath already installed. Many thanks in advance!