I totally feel your pain with the mom stuff. Our first trip to WDW was our family of 3, my sisters family of 5 and my mom, 100% arranged by me. Literally they gave me their cc and I did the rest. My mom has oxygen and can't walk far, so I arranged oxygen for the flight, oxygen for WDW,
scooter for WDW, wheelchair in the airports while wrangling then 4 yo DS. Plus I'd had knee surgery the previous year and still walk with a limp. My mom with the questions and requests in the airport and at the resort.

DH and I vowed never to travel with anyone outside immediate family after that.
LoveTripIt app. Put it on DH phone but asking me is, apparently, still easier.
Ya so far have booked Liberia to Andaz resort transfer, Andaz to Los Altos transfer, and an adventure day (tubing, zip line, hot springs) with a private guide; and a private sunset boat cruise in Manuel Antonio/Quepos. I will for sure report back if I live thru it.