Replace :

<apex:outputPanel rendered="{!IF(CONTAINS({!opp.Optional_Transport__c}, "Train "),True, False)}" >

by :

<apex:outputPanel rendered="{!CONTAINS(opp.Optional_Transport__c, 'Train ')}" >...<apex:outputpanel>

CONTAINS method already returns a Boolean value.

You don't need to add several {!...} in rendered

And you need to close you <outputPanel> tag.

Replace :

<apex:outputPanel rendered="{!IF(CONTAINS({!opp.Optional_Transport__c}, "Train "),True, False)}" >

by :

<apex:outputPanel rendered="{!CONTAINS(opp.Optional_Transport__c, 'Train ')}" >...<apex:outputpanel>

CONTAINS method already returns a Boolean value.

You don't need to add several {!...} in rendered

And you need to close your <outputPanel> tag.

Replace :

<apex:outputPanel rendered="{!IF(CONTAINS({!opp.Optional_Transport__c}, "Train "),True, False)}" >

by :

<apex:outputPanel rendered="{!CONTAINS(opp.Optional_Transport__c, 'Train ')}" />

Replace :

<apex:outputPanel rendered="{!IF(CONTAINS({!opp.Optional_Transport__c}, "Train "),True, False)}" >

by :

<apex:outputPanel rendered="{!CONTAINS(opp.Optional_Transport__c, 'Train ')}" >...<apex:outputpanel>

CONTAINS method already returns a Boolean value.

You don't need to add several {!...} in rendered

And you need to close you <outputPanel> tag.