My big ones from my first show as writer/producer, The Soliloquies of Santiago:
Do your homework on your audience, and then do more, and then do MORE: We knew there was a potential audience hungry for queer dude stories. We thought we knew how to access them. We did not do enough homework on this, and thus, we never really found a receptive audience for the show. Having the show on our CV unlocked certain funds for us - for example, the Cogeco Fund that helped us shoot the Dorian Grey trailer - but having a strong, committed fan base would have been awesome too.
Be very careful in when and whether to undermine your creative for strategic purposes: We went into Santiago ‘Act 1’ (aka episodes 1-20) with the prevailing web series wisdom of the time that more episodes and a longer release tail was better for audience-building. Alas, it didn’t end up helping us build an audience, but extending our first act did water down our creative and led to us treading water for a chunk of those episodes, plus reduced our per-episode production budget. Not super helpful.
Do not schedule a day full of intense emotional performances in long single-angle takes without adequate rehearsal: Or you will break your actors and shred your crew on an overlong day. Great actors will get it done regardless, but trust me: it will hurt them, and it will be your fault for not tracking that element.
Calm down and have fun: Even with the above hiccups, shooting Santiago was relatively joyful and painless. Do your prep, do good call sheets, hire good people, and relax. If you’ve done the right prep work, it can be a fun and enjoyable shoot for everyone, even with ambitious per-day pagecounts.
Be honest with yourself about how much you’ll be investing: My producing partner and I spent our own money to produce Santiago, and I’m still carrying a debt or two from it. This is two years later. So, yeah: it’s my philosophy to pay everyone, and I 100% stand behind that, but just keep in mind what you’re committing to - and what post-production costs you can’t necessarily control up front.