For some reason this forum is a little different to navigate and gather information than others I have been involved in.

In a situation where a tenant is non-communicative for lease renewal purposely for instance because they are navigating some life uncertainty (ie: do I take the new job?

You are in shark infested waters in the co-wholesaling world.  

I'd love to hear about some difficult situations and how you navigated them.

This guy is a wealth of knowledge on building, remodeling and everything that goes with it from finding and managing subs, to purchasing materials, to construction code and navigating the permit office, but all you care to know is how much money he makes??  

Wonderful on Shark Tank, and just tell this house... " You're dead to me"

Navigation for larger boats, ships....aesthetics? 

As a new investor anxiously awaiting her first deal I admire you for trudging through the muddy trenching of which I'm currently navigating.

I’m seriously considering this.Question/reality check: Does anyone see a downside to this scenario or would advise me to navigate the waters differently?

Unless you're writing the offer as the licensed person on the other side, hire a good Realtor to help navigate the situation and work with him (whether he's a good guy with one crappy review, or a crappy unethical one).