When did you feel comfortable to make this leap?

It's a local bank that has worked with a decent amount of flippers which must make them more comfortable with these types of situations. 

I think it makes sense to finish a bedroom first, utilize it as a comfortable "homie" space and continue with the rehab from there.

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. 

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.