Building my itinerary one by one

April is approaching so it's time to tackle a plan for a major trip. You have to read and research, then lay out a draft calendar of where to go, what to see, and when. This year I have a daily budget based on averages for 2024. Hotels.com is the default as LP no longer provides meaningful recommendations for accommodation. Factor in, also, transport, schedules, any possible senior discounts, must see sites, seasonal highlights, geographic locations, walking distances, feasible public transport, breakfast inclusions, fully stocked kitchens, no bunks, no dormitories, hidden fees, cancellation options, accurate objective reviews, so much else.
Logistics are an art and it's no wonder people go on organized predictable tours but then complain when boredom and irritations arise. People so want to avoid risk. But there is little chance of finding the singular experience that defines the trip.