So, short
question: What things should be taken into consideration while moving
from tomcat 5.5.20 to 6.0.x? Is there sort of a "migration HOWTO" for
this situation, or is it "just" rather straightforward, having
backward-compatibility and a set of new features around?


I guess it really depends on what components you are using in your application.

If you are using JSTL/JSF or plan to then, Tomcat 6.0.x is built
according to Servlet 2.5/ JSP 2.1 spec according to this chart:
http://tomcat.apache.org/whichversion.html

So, that means your project's web.xml should have the default
namespace, xsi namespace and schema location to 2.5 --- this ensures
proper evaluation of (Unified) EL

<?xml version="1.0"?>
<web-app xmlns="http://java.sun.com/xml/ns/javaee";
        xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance";
        xsi:schemaLocation="http://java.sun.com/xml/ns/javaee web-app_2_5.xsd"
        version="2.5">

</web-app>

JSP 2.1 also supports Unified EL, so one can use JSF 2.1 and JSTL 1.2
in a seamless way. I haven't really tried this but have read about it
in a few articles.

Note that in Tomcat 5.5.x the web-app is considerably different as it
conforms to Servlet 2.4 spec.

The RELEASE-NOTES document , in the root folder of Tomcat 6.x covers a lot more.

-Rashmi

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