I realize I can just wait it out and cashflow nicely, but I'd like to get the ball rolling on additional properties here at the beginning (happy to hear arguments for/against that too, btw).The solution I was thinking of was to do some sort of intermediate loan with private money until the 6 month period is over and then go with traditional lending at that time. 

What else do I need to think about, and what would a good “low ball” offer be on this?  

I then went on to explain to them though that I did not want to throw a curve ball at them as come April their rent would be increasing again and I didn't want them putting $ into anything there if they were going to have to move with that increase.

I've had no trouble attracting interested "investors" however, they always low ball me.

and not be fully leveraged to the eye balls.. 20 to 30% equity in a buyers market is NO equity.. all the folks that think they have equity.. well if you need to sell you don't.. you probably have negative equity in a need to sell situation..  

You can also use the CAP rate or income based approach to value the property if there are no properties like it, but honestly if there is another investor, broker, or agent that has worked the area for a while they could give you a ball park. 

Do it as soon as you legally can because it’s not going to get better with him and you can always stop the eviction .. better to get the ball rolling now than wait around hoping and wishing he’ll make good in his payment

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,.