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This seems like a really dumb question, but I couldn't find the answer in the rule book.

Do I have to roll separately for a unit and it's transport ? Does it matter if it's a dedicated transport ?

If they are inside the transport, no.

If separate, yes!

No, Dedicated Transports just can't start the game 9or be reserved) with any other unit inside of them.

As above. It mentions specifically that "joined" units, like IC+unit or Unit + vehicle are rolled for together

Nevermind I'm dumb.

Similarly, the player must specify if any transport vehicle in reserve is carrying any of the infantry units and/or independent characters in reserve. If they do, the unit and the transport will be rolled for together and will arrive together. Remember that a dedicated transport can only be deployed, and consequently can only be kept in reserve, either empty or transporting the unit it was selected with (plus any independent characters)

Another question though, I know the Ork 5th edition codex was basically written in 4th edition so it might be kind of screwy, but Ork Trukk's are listed as "Dedicated Transports" under the troops section. So can I just take a trukk with a tankbustas's squad even thought they can't take one as a dedicated ? Or would a squad (boyz/nobz) have to take the trukk as a dedicated, and let the tankbustas borrow it ?(and they consequently couldn't be deployed inside of it)

The second one.

The second one. The fact the Trukk is in the troops section makes no difference - it still cannot be bought by itself.