The first Spring MVC is not a configuration nightmare, you just need to know what you are doing.
To do this, I would suggest you download the Spring IDE, which has many XML editors that will make your life easier if you are not familiar with Spring XML.
Basically you need to configure 2 things
- Web.xml (it's not because of Spring it's Java EE, but you need to include some Spring MVC configurations in it)
- applicationContext.xml (here you define what you want from Spring)
- servlet-context.xml (this is also from Spring MVC and has some servlet definitions as well as some routes)
which you learn, it will be easy for you to configure and very flexible.
One note from Spring and Spring MVC are different things, I advise you to study both of them.
In addition, Spring Roo is a code generator, for Cruds, simple things and installation projects this is great, but if you need to create a reasonable large application that needs support, it will always be easier to create everything because it is easier to maintain when you know the code, so use it with caution.
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