None of those behaviors fit my definition of sweet or cooperative.Here's what I would do if I were in your shoes: if you haven't already served written notice, it's too late for January and you'll have to be satisfied with terminating their lease at the end of February.  

If you're comfortable preparing the purchase and sale contract (give yourself exit clauses for financing, inspection, clean title...) working with the title company, hiring a good inspector and negotiating post inspection etc. and have good rapport with the seller, it seems like a case where it makes sense not to use agents to me.

It's ok, I'm not complaining,  I dont want to force him into something he isnt comfortable with and destroy a friendship. 

You need to hire someone your comfortable with.

Most people don't think this way and only find comfort in a monthly number, even if it is lower.If all goes well you should have a down payment saved up to purchase shortly. 

I would recommend utilizing social media to your advantage - there are a lot of groups, particularly on Facebook, that are Indianapolis-focused that allow you to narrow in on the real estate investing market and get connected to wholesalers, lenders, and other real estate professionals quickly.I'd set up an email you feel comfortable providing publicly for wholesalers in particular - vet those you work with and be careful of daisy-chained deals. 

We have held onto some of the homes along the way and I was in your shoes a few years back when I was investing in Tampa but living overseas.

Then call brokers, pm, contractors and build a list of people so you can feel more comfortable.

We specifically look for well-built, comfortable old SFR in our target neighborhoods. 

If you were in my shoes, what would you do?