[quote=So Boerd]
Ah, I see.
[/quote]

Outcast and I have spoken about this because I attempted to make an order that wouldn't work. Here is his response (edited out vital information):

[quote=Outcast]
To land in enemy or neutral territory, you are limited to the number of transport ships you have. You can send more if you land them on friendly soil. This is unless you are sending them short distances. You cannot use other ships as transport ships except in special circumstances.
[/quote]

So basically this makes jumping points so important. Like...I couldn't land all my conscripts in North Russia, but I could in Netherlands cause of the short distance in the English channel. 

At least this is how I took from what Outcast said.