Reddit reviews Office Depot Brand Flip Chart, 27" x 34", 1" Grid, 50 Sheets, White, Pack of 2

These have been invaluable to me. I draw the significant maps out during prep and can just pull them out when needed.

1. Most battle mats and minis are not official WotC products, and they can get quite expensive. I do not recommend spending money on elaborate set pieces if you're just getting your feet wet. You can draw maps on graph paper and there are inexpensive options for minis.
   
2. This is all outlined in the free rules that you can download from the WotC website. There are additional class and race options in the System Reference Document. Those are the free resources, and I recommend you start there. You can wait to buy the Player's Handbook after you've played a few sessions and know whether this is something you want to invest more time and money in.
   
3. You can make things up as you go. This is where some of the real magic happens. :-)
   
4. Character creation can be fun to do as a group. It doesn't necessarily need to be its own session, but you should finish character creation before starting the adventure. Some players may want to spend time thinking about it on their own.
   
5. The game designers have done a good job of balancing the various races and classes. Don't worry about this too much.
   
6. That's laid out in the rules. Each class will tell you what starting equipment a level 1 character has access to.
   
7. The adventure in the Starter Set is well written. Give it a good read. During play, don't get too bogged down in the rules. If you don't know a rule, make a reasonable ruling to keep the game moving, and do a refresher on the rule you didn't know after you're done. Make sure the players know that it's their responsibility to know what their characters' abilities are, and how they work. You will have enough on your plate running the monsters.

Yea, that is about what is in my bag. I also have some incidental office type supplies like small whiteboard and sticky notes and other stuff. It is a haul.

I have an 8" android tablet with a backup battery and bluetooth keyboard. Think tiny, behind the screen laptop. I have D&D Beyond with all the books so I don't NEED all the books with me as it is all accessible.

As for mapping, I have a wet erase map and markers (kind of the medium size one) but am also apt to get the square grid easel post-it like board where I can pre-draw battle maps. But this is adding bulk and not taking it away.

Since I'm solid with the rules, my D&D Beyond setup is good enough for spell look-up. I need the Monster Manual so that will go in the bag. DMG is actually for prep time so that can stay home. If you are running an adventure then you want that book too. So the minimum is two books as long as someone has a PHB at the table handy. I have the Wizard and Cleric spell cards that are in there as well but only one set of dice.

After every game, just ask yourself, did I pull that book/item out and use it? How about last session...hmmm maybe I don't need it.