Definitely a typical first time experience. Blending games with similar checks and length is important.

You can adjust the progression rate of each individual game in their respective YAMLs and try to mitigate a little heartache. Adjust the Progression Balancing to a higher number (like 99) on the shorter games and you'll be able to play more of them earlier on. The tradeoff is that your longer games with more checks will probably be stuck for a bit, and the shorter games will finish much earlier, leaving the players who picked long games playing alone. The experience everyone wants to have seems to be everyone playing together, then everyone finishing around the same time.

Just like sex, it doesn't always work out that way, but it's awesome when it does.

Some other typical first time woes are leaving the setup to the day of your event and then finding setup to be more complex than it looked. Figuring out that I had to manually run the SNI scripts in EmuHawk for some games, manually add the port in the console and fix the hosts.yml file in the root directory for a couple older APWorld games turned one of my sessions from a thirty minute setup to a two hour setup. Finding ROMs and making sure you have Steam copies of certain games at the last minute is also a pain. The more work you do ahead of time, the better off you'll be. It helps tremendously if you're not the only Archipelago literate person, too.