*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.