DLE Den Setup: Inflexible dates, Populate calendar?

You don’t, at least not using DLE.

You can use regular Scoutbook and manually add the adventure requirements as they are completed, using the Quick Entry feature to credit multiple scouts in your den at once.

ETA: In the interests of full disclosure, saying I’m “not a fan” of DLE understates my opinion quite a bit. I got all the way through the five years as a DL without having canned meetings, and it was OK. :⁠^⁠)

ETA2: In case you aren’t already familiar with Scoutbook, there are a number of getting started links here: