New investor with 25 year tenant

[Ryan O'Hara]

Hello! My wife and I are currently in the process of closing on our first duplex in Milwaukee, WI. We are planning on house hacking, and the lower unit currently has a tenant who has been in the place for the last 25 years. Her current rent is $975 MTM for a 3 bedroom 1 bath place. She has taken incredible care for the place considering how long she has been there. However, the market rent is right around $1,500 for the place with the location and size of the unit. We have been trying to figure out the plan to make the numbers work while not making her want to leave. Our current idea is meeting in the middle at $1250-1,300. That said, what is advice do you have for increasing rent while keeping the tenant happy/understanding?