Up to this point I have worked with an agent that has their standard offer contract that they use or wholesalers that send out the contract that they want used when sharing their off market deal so the DIY approach is new to me and I don't want to make a costly mistake.  

The banks will not take an income approach and if there are no like-kind properties around, it will be compared to the nearby duplexes, regardless if they are similar in year built, condition, sq. footage, etc. 

In addition to being a successful businesswoman I have a background as an award winning interior designer/ home stager, licensed private investigator, Florida Realtor and sales / marketing expert.

He has recently approached me about a buy and flip deal that is currently off market, and he says this will garner an easy profit  of $25k after doing the necessary updates.

Any suggestions as to how any of you have approached this in the past.

While designed as a cash flow strategy, it feels like any real upside would likely come from long term market appreciation. 

I have been approached by a for profit company that would like to rent the whole house as a halfway house for substance abuse. 

I know I can't approach other people asking for their money, but if it's important, he brought up the idea of contributing on his own.

Most people will be reasonable if you approach them as a friend rather than an opponent. 

It is designed to protect the innocent and as a byproduct, the guilty get some extra time.