My brokerage syndicates it to all the sites but zumper gets the most hits.

Hey Nate, it makes sense to continue building out your investment portfolio in Milwaukee, but if you're looking in the Midwest, I recommend you make sure you get very familiar with the market you're interested in and build your out-of-state team first such as an agent, property manager, lender, and contractors if you're planning on house flipping.I recommend checking out Long-Distance Real Estate Investing by David Greene, where he takes you through how to properly invest out-of-state. 

I don't know if you can use an escalating rent clause in your area but if you have a high season I have in the past used a clause that increases rent for overstays.

I would begin marketing immediately, and mention it will be ready the date that you have very high confidence it will be available.The harder part is being selective what you show. 

Quote from @Paul De Luca: @Samuel Pavlovcik Recommended.

I am also thinking about having rental trucks on site too.

Many people online will tell you you can QuickClaim it yourself (which you can), but I always use an attorney. 

Any recommendations?

I highly doubt a day or two will cause that much of a damage.

I can't recommend his content enough.