The moisture issue and structural issue need to be addressed and you can do so before the insurance adjuster comes out.

Duplex have different zoning that may permit additional units.

One issue I see with this is that I do not have a real estate license so I don't think that would create any issues with STR management, but as for MTR management it seems like there are certain limitations without a license - any feedback on that would be appreciated-Staging properties primarily for FSBO's as I know properties listed by realtors will typically have an in-house staging offering.

There is no issue with eviction for non-payment of rent during the winter in Wisconsin.

The interior was outdated, the landscaping was overgrown, and several deferred maintenance issues were apparent.

That's the reason why we sign leases in person, so we can go over the main issues in person and make sure they are understood. 

The reason sellers cannot sell these properties through the traditional market is often due to certain issues, and 98% of the time, these issues are not beneficial to you as a buyer.

Various repair issues, bad tenant, and now this issue.

The law here says eviction is a public interest issue (of course it is!!!) 

You are micro-analyzing the minutia of each offering, but that's not really the issue.