I've created a video demonstration to show the issues that are recreatable in a brand new world via Windows 10 Edition.

DEMO VIDEO HERE:  https://www.youtube.com/watch?v=_5KtQ46hp_0

Steps to re-create

1) Create an offline world (doesn't matter which mode).  Name the world.

2) Log into world

3) Place items in inventory (Weapons, and attach armour to character).

4) Exit and save

5) Copy world save data located here:

Save data located at %LOCALAPPDATA%\Packages\Microsoft.MinecraftUWP_8wekyb3d8bbwe\LocalState\games\com.mojang\minecraftWorlds

6) Paste data to Windows Bedrock Dedicated Server v1.14.60.5 worlds directory, and rename directory to match world name

6) Modify server.properties to reflect test world name

7) Launch game and enter in world under Servers tab

8) Notice discrepancies of items worn as well as inventory do not reflect those in local world.

I've got a bit more detail with screenshots to this issue, but opened the bug in wrong Project, should have been opened here under BDS not Bedrock Codebase (unless it is related I suppose).

In reference to this report: MCPE-75064