I’m not sure why you say it’s for business. I do a lot of business and personal travel and it’s great for both. Organizing trips with friends and family is much easier to coordinate with tripit and my boss couldn’t care less which hotel/flight I’m on.

The pro features specifically is mostly just alerting, not tied to personal/business.

I have never used the sharing features much. I say business but perhaps what I mean is frequent travel. I.e. having enough flights and hotels on your calendar that they're hard (or at least a bear) to keep track of.

There are still folks that recommend AAA memberships for leisure travel, and that start at $52/year (plus "admission/activation fees").

On the flipside, I see so many people these days using a wild combination of improv wandering, personal recommendations from Uber drivers, Airbnb (or VRBO or whatever), and Yelp, that I think a lot of leisure planning has gotten sometimes too weird and undirected/semi-directed versus classic trip planning models.

Weird, maybe. I would say that relying on Yelp or Thrillist or Eater or whatever is the top result on Google still ends up with everyone crowding the same (weird) places.

Not much different from traditional trip planning though, if you are just swapping from "top AAA recommended" (or "top guide book recommended") to "top Yelp recommended". Having a person involved in something like a AAA trip plan added some variety in terms of inter-personal suggestions/customizations. (Or specialized/niche guide books.)

Arguably Yelp has a massive (maybe a bit stalkery) version of that inter-personal suggestions/customizations at your finger tips in that you can come to get a feel for individual reviewers, especially area Elites, and how well their tastes align with yours. It is possible to find interestingly curated lists of places in an area if you work at it, which isn't that different than the guide book era (though maybe weirder). Certainly not as convenient as paying someone else to do all that trip planning work.

I've been using, mostly, travefy, and haven't had the time to check Trip It (I think I tested it years ago, and had something I didn't like)

Is it better?

It hasn’t changed noticeably in the better part of a decade. But it works really well for me (albeit not the prettiest app in the world)