I have a few rentals with section 8, and they are professionally managed.

As someone who occasionally works with these investors, I always try to emphasize the challenges that come with real estate like managing renovations, dealing with tenants, and navigating market fluctuations.

One reason was the condo management company wasn't doing a great job and there were always extra levies. 

Managing a rental (even if it cash flows) comes with responsibilities, and it might not be worth it for $300 a month.

Reach out to Lisa Loesel at Short & Suite Management here in Milwaukee. 

Practical Tips for Managing PropertiesFinding Good Tenants: Screen thoroughly.

The key is building a reliable local team—property managers, realtors, and contractors you trust.

It also includes managing your existing investment well to ensure you aren't bleeding money due to bad tenants, excess maintenance, etc. 

It would also be much easier to manage considering you are currently living in Arlington.

As a management company, we also have a duty to get a property occupied with a qualified resident as soon as possible and sometimes that means adjusting rents down for right now to generate revenue.