I meant to reply sooner, but the afternoon got away from me while I was finishing a few things around the house.
For the garden question, I would definitely move the smaller pots together first and watch how they do for a few days.
That usually makes it easier to tell which spot is actually helping and which one only looks better at certain times of day.
I also think trimming just a little at a time works better than doing everything at once, because it is easier to notice what changed.
If the weather stays mild, this weekend seems like a good time to clean up the leaves and start fresh.
I am happy to stop by and help for an hour if you want a second set of hands.
Otherwise, send me a quick note after you rearrange things, and I can help you think through the next step.

I think keeping it simple is best, especially if everyone is already tired from a long week.
Maybe start with a short walk, then decide later whether you want to turn it into a bigger outing.
Sometimes having a flexible plan makes the day feel easier and more relaxed, and nobody feels locked into one thing.
I also liked your idea of bringing a blanket and a small speaker, because that seems like enough without making it a whole production.
If the sky looks uncertain, you could switch to that indoor place you mentioned and still keep the same easy pace.
I am good with either option and can help pull a few things together tonight so tomorrow feels smooth.
Just let me know what time sounds right, and I will adjust around it.