The tenant also say that they requested time off work to move and have delivery the first few days. 

If you aren't paying off the existing $25k, are you going to "subject to" it?

In my experience, if you don't have that edge, you will likely struggle at active investing and you are better off in syndications.

I put too much into renovations because of the classic found a bad contractor story, so had to get another contractor out, and after 9 months holding cost and about $60K in repairs, $3K in appliances, I got the place rented. ( I also refinanced and was able to get about 133K out, which I paid off my HELOC and credit cards I used to pay for all the renovations and PP). 

Have you considered starting off with a primary and house hacking?

If your looking to generate off market distressed seller leads, then I would look into Investor Carrot. 

I am trying to find off market retail commercial deals.

Once construction is completed and townhouses are sold I will pay off the seller I financed the land from.Is this feasible?

Are you moving in order to invest or simply moving and want to Chicago and want to start off by buying a property? 

Looking at single family or a duplex to start off the adventure, then sky's the limit after that.