I'm guessing that your popup is a bit better appointed than the one I just moved out of. i had a Rockwood 1910 Freedom with power nothing.
Power tongue jacks and poper roof lifts would make things much easier I'm sure....
I did quite a lot of one night trips in her, but came to realize that it was just too much work to do that, in our opnion. So we tried to make our trips 2-3 nights.... and even then it seemed like a lot of work to me after a while.
I always wanted to make a week long trip someplace, but never made that happen.
I think what you are planning would be a lot of fun, but i would plan on keeping the set-up minimal, both inside and out.
I would probably try to stay in each spot a minimum of 3 nights.
Awning maybe not at all, camp chairs maybe, but no tacky lights, no patio rug, no tables, etc..... especially for one or two nights
only bring along the minimal stuff in terms of clothes, cooking wear, etc....
I would try not to unhitch as much as possible.
and I would probably plan a night here and there in a hotel as Sam suggested to break it up for DW's sanity