Looking at the listing of DLC for TSW5 on Steam, it indicates any route that you already have in TSW4 as ‘in library’, with the exception of Blackpool Branches (which I do have for TSW4) which doesn't show the ‘in library’ indication. Every other DLC that I own on TSW4 appears to be listed correctly as ‘in library’ Just flagging this up as a possible link error in Steam, or similar.
Probably the according paks have not yet been recompiled for TSW5 and are "locked". They have a few weeks still for finishing the launch preps. Not saying it could not be an entitlement transfer error though, maybe DTG-Chris can check. On my end, Blackpool Branches and West Cornwall Steam Railtour are missing. The rest is complete and awaits download next month.
There were several of my DLCs not showing as owned last night but now seems to have been corrected except for West Cornwall Steam Railtour. If it's entitlements that is the issue then this is only going to get much more complicated in future years as a "new" game has to have more dlc linked back to all the previous iterations.