I'm curious: What purchases or services consistently force you down similar rabbit holes despite having clear requirements?
Some examples that might resonate:
"Finding a laptop bag that fits my specific model, has enough pockets, looks professional, AND has a good shoulder strap means ordering and returning 5 different options"
"Trying to find restaurants that are vegetarian-friendly, not too loud, take reservations, and within my budget means checking 5 different apps"
"Planning travel where I need specific weather, budget constraints, activity options, and flight times requires dozens of tabs and constant recalculation"
"Finding fitness apps that know my equipment, adapt to my schedule, consider my injuries, and align with my specific goals is virtually impossible"
"Apartment hunting with filters for pet-friendly, in-unit laundry, <30 min commute, and under $2000 still means clicking through dozens of listings that don't actually match"
What's your "I can't believe this is still so time-consuming in 2025" category? What specific requirements do you have that make the search process frustrating?
I'm analyzing patterns in consumer search frustrations and will compile the insights from this thread into a blog post to share with the community.
A couple of the queries you've listed are a bit of a big ask such as "Planning travel where I need specific weather, budget constraints, activity options, and flight times requires dozens of tabs and constant recalculation" - not that doable as an ordinary internet service as IMO it is just too fluid unless the region you want to visit has very stable weather patterns - no doubt in the future there'll be a travel planning LLM to help streamline a road / air / train trip.
The chase finding specifications is a pretty good reason purchasing / procurement offices and the like have their job. It is though a peeve of mine that much of the net is aimed at ordinary folk, and as such so much of those authoring the web page for an unique item seem to miss including a decent list of specifications directly on their web page. A plain list of text of 10 - 50 points beats some external or clever BS that doesn't.
Much of the issue with somewhat meaningless searches is the content in a given website is somewhat lacking. Present times it just seems like amateur hour or the people behind the site thought they saved money by using some cheap as chips means to create their site. They seem in situations where there are requirements or prerequisites, forget it might be useful to list them, if the item has features, why not list all of them as well as point out if for some reason the item doesn't have a function ordinarily expected. I also find too many of service oriented areas are merely a large about blurb.