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

When I started in WA DC area funding a few new projects..

They got into escrow, and then the tenant started to create a real challenge for the seller and ended up taking them to court for performance/lot line issues on the property.

This allowed Jerry Scott and Chad Wolfe to focus on the execution of the project without needing to invest their own capital upfront, ensuring a streamlined process from start to finish.

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!

@Robert Kline, I would start by talking with your local building department. 

Our team along with clients all are heavily investing in the area, and it is a strong place to start. close proximity to New York and New Jersey, paired with extremely affordable property/taxes and high rental demand make it on most people's radar.  

Not sure if there's a lesson to be had there, but that's how I found it.I'll say though that once you know what you're looking for and create an industry specific network, you start to find them with some frequency.

This might he the start of a new niche to take advantage of.  

You should have already started the eviction process!