I responded to your DM, but it's basically what @Chris Seveney said.

My goal is a win-win situation, and it's basically for him to do owner financing and rent. 

Ok, so basically if you have your 25% downpayment you can just go buy any property off the MLS.  

Part of that you can justify because of the necessary repairs, but overall higher price points appreciate differently.The median home price has basically doubled in Milwaukee from about 160k to 320k in the last 10 years.

If it's your first LLC, though, it might be wise to work with an attorney to guide you through the setup process and some basic steps to take afterward.

You can offset the passive losses from one rental against the positive income from another rental.Therefore, you will likely have a net $3,000 loss across all the three rentals which you would carry forward.If your depreciation was more than $3,000, you basically made cash-flow or rental income that was not taxed, which is good.Best of luck

Now after the fact, he sends us a bill that basically outlines taking care of all the same things the other bit mentioned, but he is  wanting 23K after the fact.  

But as I got more experienced I learn less and less from most forum posts are you know most basics already.

They are two different methods and there is a ton of content out there on both.Seller financing - the seller basically becomes the bank.

You are basically building a new home on a piece of land.