I saw this thread and had to jump in because I just went through the exact same OBX planning drama last year with 18 of us! It was total chaos until we figured out what actually works. Re: "> TimeTree mentioned a few times but I..." - honestly, you are so right to be skeptical. I am obsessed with getting these things right, but TimeTree was a total disaster for us once we hit 12 users. It would lag so bad that my uncle would enter his dates, and it wouldnt show up for my sister for like three days. Total nightmare when you are trying to book a house! One major thing to watch out for is any app that requires a login for every single person to just view the schedule. That is a massive trap! My older relatives literally lost their minds trying to remember passwords and it basically turned into me being a 24/7 tech support desk. Whatever you pick, make sure it has a simple view-only link. I am a huge fan of using something more robust like Planyway or even just a well-organized Trello board. I love it because you can see everything at a glance without the calendar clutter that makes Google so messy. Just a heads up tho, be super careful with anything too lite because they usually strip out the notification features you actually need to keep 14 people on the same page. The sync lag on most free apps is the biggest danger. One person thinks they have the week off, but the app hasnnt updated the master view yet... it is basically a recipe for family feuds!

> TimeTree mentioned a few times but I read some reviews saying it glitches out Teamup is super reliable and im happy with it. Do you need a free app or is a small fee okay?

^ This. Also, you gotta watch out for hidden costs with group apps. Many planners cap free users at 10, so with 14 people you might face steep per-user fees. I usually suggest Trello because it stays free for basic boards, but avoid anything that forces every family member to set up complex profiles. It just leads to more tech support calls from your aunts later on.