Additionally, it needs to be filed in probate court.

Its hard for you to claim in court that you didn't intend 10 days.

It’s 4bd 3.5ba nice neighborhood and planning to cover inground pool and add pickle ball court.

Neighbors are unlikely to show up in court to testify, plus they may have another beef with the tenant that biases anything they say and you may not know that. 

It seems pointless to try to sue someone in Japan which is where the owner lives.Get the city to bring a public nuisance suit, and have it ask the court for power to abate the nuisance, which can be as little as board up and as much as demolition of the house. 

Most landlords in Milwaukee own less than 5 units and it is not a big focus in their lives, they are not on BP, they don't belong to the RPA etcIronically, for a couple bucks you can get a court-tested lease from Wisconsin Legal Blank or from the WRA.Court rulings like this also mean that it will make the market tighter for tenants as landlords are driven more and more into defensive strategies.

The laws are not landlord friendly at all and it's common for landlords to get stuck with a non-paying tenant or squatter and have to legally keep paying the utilities, taxes, mortgage, etc. while the eviction gets delayed in court for months or years.

You see, there’s nothing worse for an attorney taking on a contingency case, fronting all the legal expenses and investing their time to win a case and obtain a court judgment – then NOT be able to collect on the judgment.So, astute attorneys will research the available assets and insurance before accepting a case on contingency.

I'm worried that if I ever need to involve law or courts for anything like eviction or collections, if/how that would work.

The city has high taxes and free lawyers available at the court house.