By giving myself this permission, it made the MeetUps less anxiety-provoking since it was possible to meet someone in the first 10 minutes and then I could leave.

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If someone moves in with your tenant with or without your permission or adding to the lease, they have the same rights as your tenant. 

For example you could charge for linens, or for electricity, or permission to sit on the couch, or a portion of the property taxes.

I went to see this property with your permission.

Jordan,I am not too familiar with tenant/landlord laws in WI but in Oregon you would have to seek permission to come to the property to do that, 24 hour notice each time.

Remember, when the Seller signs the deed, you become the owner of the property and you would then have to turn around and give permission for the Seller (who at the time no longer owns the property) to make repairs.  

I think it’s a great idea to maximize your return but I don’t know if it is *technically* permissible.

He's not on the lease, but he was occupying the property with the knowledge and permission of his girlfriend, so he has rights.Start the eviction process.

The "ask for forgiveness rather than permission" strategy is beneficial to many cases, but township zoning departments is not one of them lol