Consult a CPA to ensure compliance with tax regulations and explore strategies that align with your goals, such as providing for your mom while managing tax implications effectively.This post does not create a CPA-Client relationship.

Vitaliy provided some great points about the pros and cons of single family verse multi-unit investing.

In many places there are some utilities provided by the municipality.

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!

Its hard to find deals unless you are connected, advertise a lot, cold call a lot, knock a lot, and/or work very hard at it. 

You should be able to find local builders that will finance the construction component of your new build, however! 

Can the agent provide comps?

Could VRBO users from Michigan provide some clarity about the topic of sales tax/lodging tax collection and payment to the state.

While I’m open to both turn-key and fixer-upper properties, my preference leans slightly toward value-add opportunities where I can improve the property and increase equity or cash flow.That said, I’m also happy to consider turn-key options that provide immediate cash flow if they fit within my investment strategy.

I've been buying and renting here since 2009, the deals are hard to find these days but definitely out there!