Making my list, checking it twice

Packing for our month in the city is a little daunting. It's not quite packing a few outfits for a vacation, but it's not packing up and moving, either.

I'll need casual clothes, party clothes, interview clothes, workout clothes, a swimsuit or two for the pool and hot tub ...
But beyond wondering exactly how many pairs of shoes to take, I get visions of lugging eight steamer trunks when I think of the provisions of daily life.
We love to cook, so we'll need to take at least a few of our favorite cookbooks. Should we take coffee, tea, spices, sauces ... the effort and expense of outfitting a second kitchen seems daunting, but so does taking it all with us.
Ditto for a bathroom worth of toiletries. I usually travel with a hanging toiletry case, but my mini bottle of conditioner won't last for a month.

We're really lucky that Ben and Gabrielle are leaving their printer, their cat's litterbox, even a bike, so we'll have several big, clunky things that we don't need to drag with us.

It looks like our friend HT might housesit for us while we're gone, so I suppose worst-case scenario, if there's something we forget and just can't live without, we could always ask him to UPS us that warmer pair of mittens or a string of Xmas lights.

Anyone have any advice on how to manage the balance of too much/ not enough stuff?