Check-In and Check-Out are two different events in a Travefy itinerary. You can select the option to automatically have a Check-Out event made when making a Lodging Event from the database, but if you want to make a Lodging Event manually, you can still add a Check-Out event!
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First we'll go over adding a Check-Out when pulling information from the databse, and then we'll go over creating one manually.

When in an itinerary or proposal, click on +New Event

A list of events will appear. Click on Lodging!

You can type in the name of the hotel you're looking for in the search bar, and some options will appear!
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You can see in this picture, that there are three little bubbles that appear at the top of the search. Those in green show the databases being searched!

Clicking on one of those bubbles will change it from green to white, signifying that it's not being searched in that database. See below to see only Library selected!

After making your selection from the database(s), you can specify the check-out date. That will determine what day the Check-out event will appear on!

All that's left to do is click on + Add to Itinerary!
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Go to the appropriate day, and click on +New Event, and then select Lodging.

Add the information you want to appear on both the Check-In and Check-Out events. This can include the hotel Place attachment, photos, a title for the event, etc.

Click on the More button (...) in the bottom-right corner of the event, left of Done Editing. A few options will appear, click on Duplicate. This will make a duplicate event!

Click on the Pencil icon in the top right corner of the duplicate event to edit it. In the Type section you can change it to be a Check-Out event.

Simply drag and drop the event to the appropriate date!