Falcor_Rowlinson

So I've been browsing around and just wanted some feedback from anyone who cares to take the time, there are quiet a few organisations (including my own) that are based around some sort of player provided service from military/security to hired labor. My questions to everyone are;
 
1) What would level of player interaction would you be willing to pay for?
 
2) How would you ensure you received payment?
 
3) If you were paying someone to transport or deliver cargo would you feel entitled to some form of 'insurance'?
 
4) Would you gamble in-game with in-game currency (if any large faction leaders are reading this, would your empire outlaw gambling if only for roleplay purposes)?
 
5) What in your mind makes a service provider reliable?
 
I realize some of these may be obvious, I intend for  this to spark a conversation rather than just simply answering the questions. I have thought up my own responses and would like to discuss them.
Also if anything here is 'common knowledge' and redundant I apologize.

Introduction:
Oh where to start... My name is Falcor Rowlinson, yes like the luck dragon I've kept the handle and organization name from back in EVE at its pinnacle TDN was still a small corp of around 30 - 40 people typically dealing in logistics for local pirate groups and contract work. As of now 7 or so years later we're still a small community that primarily plays Arma 3 as a semi - sci fi private military.
 

Operation Conquistador, 7/21/2035
 
Plans for DU:
While only myself and one other from the community are taking part in the alpha others will be following in whenever the game is ready, Our goal is to form a PMC with an integrated weapons company as well as establish a 'neutral ground' location (eg. Night Club, Bar, or Casino) that exists outside of any groups sphere of influence to be a safe haven for the less than ideal citizens of the local space to handle their business whatever it may be while still having the sense of safety provided by a local security force.
Contact Us:
Teamspeak: ts01-nyc.nitrado.net:10050
Email: Todan.Corporation@gmail.com