If I do go this route, I will obviously give the current management company notice (after reviewing the contract), but are there challenges to be mindful of when switching Property Management companies from afar?

Well, if you can say it with a straight face, then you avoided recapture tax.Problem 2.

Quote from @Maya Jones:  Newbie landlord faced with applicant that wants to live with his cousin. 

Otherwise, they will abuse the relationship when they face a financial challenge.Tenants never want an increase in their rent, but winter might be a good time to increase rent as there is typically less inventory on the market and who wants to move during the Holidays?

You meet face-to-face (or Zoom-to-Zoom).

.👉 Curious — what’s the biggest challenge you faced when setting up your first MTR?

Since you no longer live in Wisconsin, you may face state income tax considerations both in your new state of residence and Wisconsin, especially if you generate rental income or take deductions on the Wisconsin property.You could also explore passive investing with partners in larger properties to grow without managing everything yourself and these don't have to be local.

Our notices go out 90 days prior to a N/T Sale, so if you pull notices that were sent out this week, you will get leads for people that are facing foreclosure in about 90 days. 

What challenges have you faced when structuring these deals?

You can personally vet properties, meet your team face-to-face, and handle any initial issues that arise.