I was just getting the rest of the footprints set up and that also involved selecting what sort of connectors and buttons do I want. I hadn't really been thinking those before and of course its another rabbit hole again. 

First the simpler one; switches. Most ESP devboards I had seen did feature a pushbutton for entering programming mode, that you are supposed to hold down on boot. I began to think that maybe having a slide/dip switch would make more sense, you wouldn't need to fiddle with holding buttons down as much. Continuing on that trail of thought led me to the idea that using SPDT switch (instead of simple SPST) would allow me to remove the pull-up resistor from the pin; the switch would always connect the pin solidly to either Vcc or GND, so no floating around. That's nice win, especially as I'm not 100% confident that my great idea of minimizing BOM and using same 249k resistors would actually work that great as pull-ups as they are bit high valued. The downside of using slide switches here is that now I need to order two different types of switches, pushbuttons (or tactiles) for reset and slides (or dip) for programming. I think the tradeoff is worth it.

The power connector is another issue. I had been thinking just using "some generic power connector", but of course there is no such thing as standard common generic power connector. I could put in 0.1" headers in, but those are not really ideal as connectors and they are kinda bulky too. Quickly googling around people seem to be using among others Molex PicoBlades, whole variety of JST connectors, and I also saw some Hirose DF series ones. They all seem pretty much the same to me. I suppose JSTs are most common (?), but there are also like 10 different varieties so that's not all that helpful. I probably will go that route anyways, but I'll need to do bit more research still.

These are the things that are keeping me awake at nights now. And I was naively thinking I would be getting to PCB layout anytime soon..