I will add that you definitely do not need to be near your investments, but it makes things a lot easier when you first start off. 

You should have already started the eviction process!

The property was occupied (still is) with 1 tenant that I am now having the exhausting pleasure of evicting. 2yrs later, said tenant continues to try every angle to delay the court granted Marshall’s execution.The “2nd” floor was poorly renovated (bad contractors), new tenant moved in and a year later, another eviction process has started as they lost their job and refuse to move or pay.Stuck with a very large mortgage bill (that I am paying), utilities and making small repairs to keep the property up also noting the casual 311 complaints from both tenants. 

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

Quick heads-up: Starting January 4, 2025, Pennsylvanias Act 52 requires anyone involved in wholesaling real estate to be a licensed agent.

I'd feel comfortable investing ~$50k to start off.

I want to make sure I screen tenants properly, but I am not sure where to start.

There is already at least one request with a lot of votes for this feature, and you can allocate your "votes" to it as well...maybe Buildium will start work on it after it gets a few hundred more votes. 

I would start at paperstac and Brett Burky and Co. 

If you just hire the cheapest or first PMC you speak with and it turns into a bad experience, please don’t assume ALL PMC’s are bad and start trashing PMC’s in general.