Short and sweet, put the ball in their court.

Suddenly the tree shading their windows is cut down, there are leaf blowers going at 7 am on the weekends, water shut offs 'for maintenance', etc.The issue here is that whatever his play is (and it doesn't matter what it is), you are along for the ride because your only remedy is lawsuits if he's not playing ball. 

We are looking to start March 2019 as we will have 50k saved up to start.We have have solid jobs in Chicago and are looking at Milwaukee to get the ball rolling,.

It has message boards and to do lists so every party knows who has the ball. 

Yep, that's in the ball park.

You'll get some additional benefits with a CSS if you replace an item as you'll be able to claim loss deduction, and also your heirs might benefit if they inherit a property with CSS (too bad you have to die for that though).And then there is the question of the value of money now, vs in the future, or the future value of invested tax saving.So, now that I gave you (most of) all the balls, try and juggle them all in the air and see how it goes for you.I can tell you I choose to spend the money and get CSS for two of my SFR rentals.

That’s precisely what I did with my fiancé.

Some subordinate mtg lien holders play ball by 1st mtg investor guidelines and others don't. 

It's not turning a profit yet, but in the meantime here's a bunch of business, travel and equipment expenses we would like to write off")2) Did I completely drop the ball not putting this thing in a self-directed IRA?

I do not feel that is likely that things will sour in the future, but I don't have a crystal ball.