How does starting on a smaller 1 to 1 scale to start with. With one of the PC from that Party and see how it goes?
[IMG]https://i.imgur.com/AdB7NYU.jpg[/IMG]
With the starting setting for the game being either Waterdeep on the Sword Coast of the Forgotten Realms.  Or either City of Greyhawk or Verbobonc in the Greyhawk Setting.  Or any large city in a homebrew setting. The PC I want to play is known as Fenix the Fox, the male Halfling/Hin Rogue, with the Urchin background. Starting out in the main city. Having fairly recently left his urchin street gang, (Think 'Oliver Twist') and became a probationary member of the city's Thieves Guild. Where all members must turn in the items they have stolen over a value of 1 gold piece. So the the Guild can take there 40% cut. Fenix being a bit of a stubborn fellow did not do such, one time. Another Guild Member saw Fenix admiring the item when he thought he was alone. An of course snitched on him. Punishment for such was to be beaten within a inch of your life and have the Guild take a 60% cut of what you stole there after. Thus one day Fenix noticed that he was being tailed by one of the Thieves Guild Thug squads. So leading them into what appeared to be a blind alley. As he got to the dead end. He turned and asked what this was all about. They told him and not wanting to pay the price. Fenix escaped by squeezing through a halfling sized bolt hole that he knew was in the wall there. Going to ground down in the sewers. Until he came up with the plan of stowing away in a freight wagon, that is one of nearly a dozen in a caravan that was leaving the and heading out on one of the major traderoads that ran from it. The further away the final destination is, the better.  As far as Fenix is concerned.  Then over time, through a series of adventures and misadventures.  Fenix comes to know the other members of the Party that I first mention.  How does that sound?