Where To Begin A Dungeons And Dragons Game?

Beginnings are always difficult. This is no less true for a Dungeons and Dragons game we've planned for this weekend, to celebrate American Thanksgiving with some friends.
I've two places from which to begin the adventure: one, a decadent, crumbling city in the throws of an economic slump; two, a small town on the borderland, surrounded, on several sides, by ancient ruined cities and temples. Depending on which place the game starts will affect the tone of the game. If it begins in the city, we start with a bustling, urban feel to the game. If in a town, the tone is bleak, windswept, insular and isolated.
The city gives us more opportunities for rumours and varied character backgrounds. But the town provides more focus, as is easier for me, the DM, to manage and circumscribe the adventure options.
The outdoor map, above, is a small slice of the 1981 Dwarfstar Games Barbarian Prince game map. Barbarian Prince is one of the microgames that I always wanted to own, but found far too expensive in the resale market to justify purchasing. Fortunately, you can download a free digital copy from the above link, courtesy of the games licenseholder, Reaper Miniatures. Over at Sigils & Sinews, the author is running a solo Barbarian Prince game which I am following with interest.
The Barbarian Prince digital map is one that I can appreciate and would prefer to employ in my games, since it uses the sort of mapping style that I prefer, and the digital map can be printed at a resolution that makes it easy to add notes and icons to the map for quick reference. The Barbarian Prince map also uses a hex id system (similar to the SPI or traveller subsector maps) that allows one to keep separate notes on the contents of each hex.
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