I have 2 old iPhones sharing same Apple ID and I need to transfer everything from both phones to my new iPhone 14 before I turn in trade in?

You have two iPhones with the same Apple ID inspite of this there are many data which are device specific.

Most of the App data are device specific

If you turn on Messages in iCloud, iCloud Photos, Mail, Health data, call history under iCloud, and files you store in iCloud Drive your content is automatically stored in iCloud and is available on all devices that use the same Apple ID

try transferring data manually. One by One

1. If your old iPhone had iCloud enabled Optimised storage enabled then please do the same on the new device too. Check if you have enough iCloud Storage if you are using another Apple ID.
2. Messages, Media, Voice Memo, Keychain --> Turn on Messages in iCloud & iCloud Photos, Voice Memo, Keychain, and your content is automatically stored in iCloud and is available on all devices that use the same Apple ID including iCloud Drive
3. Contacts --> Contacts are not stored on an iPhone nor on SIM, they are synced to  Google, iCloud, AOL, Exchange, Outlook, Yahoo or any Other. Use the email account that is in your old iPhone.
4. Notes, Reminders, Calendars --> You may sync all these from any of the email accounts that you have on your old iPhone. they can be synced using  Google, iCloud, AOL, Exchange, Outlook, Yahoo or any Other.
5. Email Accounts --> Add them in the iOS mail app manually one by one. If the email accounts were added through a Profile added by your organisations then you need to contact your organisation's system administrator or --> Install or remove configuration profiles on iPhone - Apple ...
6. Any Specific Files --> Upload to Cloud Drives (iCloud Drive, Google Drive, OneDrive, DropBox, Flickr, box, AmazonDrive, Adobe Creative Cloud and Use Files app on your new iPhone too.
7. Apps & Settings --> In any way they have to be redownloaded using the App Store. Even you had used any of the 3 processes mentioned earlier. Apart from the Apps following will also not get transferred.
   1. Content from the iTunes and App Stores or PDFs downloaded directly to Apple Books
   2. Content synced from iTunes, like imported MP3s or CDs, videos, books, and photos
   3. Data already stored in iCloud, like iCloud Photos, iMessages, and text (SMS) and multimedia (MMS) messages
   4. Face ID or Touch ID settings
   5. Apple Pay information and settings
   6. Apple Mail data
   7. Apple Music