I recorded some videos of OCTGN league play a few weeks ago, and finally got one uploaded. These assume you have a basic understanding of how to play Doomtown.
Let me know if these are at all helpful!
This particular game is my 108 Blessed vs shekky_ducky’s Desolation Row. Went a little over an hour, but it would have easily been less than 55 minutes had I not been talking strategy/thoughts. Ended up being a very good game!
Great video so far - and a great example of why you might not want to go into a gunfight round 1 with your extra even though it only costs you a GR!
Aaand the danger of staying in a shootout with no cards in your hand!
And for the bit more strategic discussion - why didnt Sloane stay for one more round of the shootout after the round he lost, when he knew he was going to draw his joker in the next hand? (41:00)
On why you may not want to go into round 1, even if its only a 1 GR chump: I was probably wrong, here - that’s 2 casualties I didn’t have for later fights with important dudes, and even if Jaels was free, its still a lost cheatin’ res goods (although shekky basically never cheats, so its not as good against him).
Lesson learned: throwing away any dude, even if that dude was free, is not smart. Exceptions include: if you have a chance to inflict some real damage, or if you can get rid of some shootout or cheatin res cards from their hand for a follow up fight.
I’ll save the 3rd question for @shekky_ducky 
That’s an easy one: I didn’t realize that. I was focused more on my empty bag o’ tricks than my future draw hand. As Pr0digy points out, without cards I am nigh powerless.
Locally or online, it’s ‘know your opponent’.
One of my locals plays base Lawdogs plus updated tech (Judge Harry, Faster on the Draw, etc.). I know he’ll tend to avoid shootouts until he has a Sun in Yer Eyes or a Pistol Whip to dictate the terms.
Where have I heard that phrase… ‘Play the man, not the game…’ 
Which works fine untill you sit in a foreign country with opponents you dont know
That’s when you start reading their lowball hands and discard pile a lot more than you usually would to try and figure out their plan
Follow up to #4, the next one plays the same deck (PTPT Slide) but against a less crazy aggressive deck: https://youtu.be/zGbNaVFi7T4
aka: Playing Other Peoples Decks Poorly!
Great game showing how you can win shootouts, but still narrowly lose the game. This is why I love Doomtown!