1. How do I approach the title company regarding this transaction?  I was turned away from one title company because I told them what my exit strategy was in trying to wholesale bank owned, & city owned property is 'non assignable' hurdle. 

They mentioned they would need a lawyer involved on both ends to assure there's nothing illegal going on. 

2. When resining as trustee and adding the buyer as a beneficiary, & a non refundable earnest money is required this brings me back to my first question, how do I approach the title company without any red flags. 

the way I've learned is there are three documents that are needed..... Purchase Contract, Resignation as trustee & 100% beneficiary rights resignation.... 

what am I missing? how do I successfully handle this transaction. 

Find a lawyer in your area that has a title company and understands trusts.