*EDIT*
I've created a video DEMO to show the issues that are recreatable in a brand new world. DEMO VIDEO HERE: https://www.youtube.com/watch?v=_5KtQ46hp_0
If you take the following world download file (see link below):
https://1drv.ms/u/s!Aivrh6gXIbxkgWyxIhGy67dmJzvn?e=pqtntk
...and import it locally and play, you'll notice that the world loads fine. Items including the enchanted sword are perfectly in tact.
Within Win10, after importing the world, copy the "Meadowview" directory world save data from %LOCALAPPDATA%\Packages\Microsoft.MinecraftUWP_8wekyb3d8bbwe\LocalState\games\com.mojang\minecraftWorlds and place it into your Windows based Server folder, bedrock-server-1.14.60.5\worlds directory, configure server.properties to use "Meadowview" as the world name, and launch the server, the world loads but is loading an older state of the world with missing in game items, items, different logged out location, etc.
Server download link used: https://minecraft.azureedge.net/bin-win/bedrock-server-1.14.60.5.zip
I've attached 2 screenshots, one with the local world loaded, and one with the world loaded into the Windows based 1.14.60.5 server.
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Putting your items in a chest is, at best, only a partial workaround. You also lose control of you pets (as mentioned by a commenter on BDS-5121), and you lose your levels.
We're tracking this issue as BDS-5121, so this ticket is being resolved and linked as a duplicate.
If you would like to add a vote and any extra information to the main ticket it would be appreciated.
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Copying an explanation I wrote in another report.
When you play a world locally you are considered the "local" player - that player isn't specific to your account, its specific to the world. Its why a streamer can upload their world with items on the player and they show when you load up the world. However when you play on a BDS everyone is considered a "network" player. I'm assuming changing this would break worlds for people that play with no network connection etc. Your stuff is all still there, if you move the world back to a local instance all your stuff will be there still.
To work around the issue you need to place all items in a box before you transfer the world over to BDS.
Ionic