If you told him you have been playing pickup games for the past year and need help improving your jump shot, now he has evidence you're motivated and a specific goal he can quickly help you work towards.

He played dumb, telling me he told me from the get go that the initial inspection was all we were getting.I would have never taken the deal if that were the case!

I thought of banking on appreciation and rate drops as pure speculation and akin to gambling.

If your network likes the pure equity play, you should offer that.With the "debt" financing, are you planning on using this as your mortgage, with no "traditional" mortgage ahead of it?  

Do I know how this will all play out ? 

I chose to mention grad school because it plays a big decision in my first option as well.

Just eliminating some perks for the folks that don't play ball. 

I do this so I know what Im getting into and to look for additional value added play... and if I can find ammunition to negotiate price down.If you are not experienced walking the site, always bring an experienced GC.  

Then when you get tenants, differences in personalities clash and playing middleman is rough.

Interest rates will play a huge factor.