Colville suggests that starting in a tavern is a chance to show off the setting in a microcosm. Put folks there that represent various factions or attitudes prevalent in the setting. When I ran a Savage Pathfinder game and had my players start in a tavern, I had some incurious off-duty town guards, the dillettante son of the mayor. I couldn't figure out a way to work in the diabolist church (I set my game in Cheliax), but I did have a choice of several "first jobs" for them to take.
Me too, I backed the project but I'm not on the Patreon, so I gotta wait for my packet, lol. But if James was right in the last Q&A they posted to the YouTube, it should be out sometime next month!
The "Help" action is so lackluster in D&D 5. I appreciate that it exists that IS certainly a step up. But you do nothing with your turn (not very exciting), and your friend has Advantage, which helps, but if I had a nickel for every time I failed a roll with Advantage, I could probably buy a new copy of the PHB.
(Only a small part of why my game of choice is something completely different.)
It's such an odd game. There are some genuinely interesting dichotomies at play, a lot of potential for good drama, and themes I like, but it is not easy to wrap your head around, and moreover the book feels like it was laid out by an actual faerie. Which is kinda atmospheric, I guess, but you could, you know, impose some organization in the character building sections so players can find stuff.
My wife (girlfriend at the time) ran a short campaign for some of our friends a little over 10 years ago. It was fun, but damn. Building a character was such a headache.
Absent knowing anything else, and assuming most of the "usual" fantasy tropes are in place?
Either Savage Worlds, or Colville's Draw Steel depending on how I feel and how my upcoming experimental play of the second one goes.