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The requirements for this web app include the following:

1- Need to interact with a couple other websites that don't necessarily have any type of API, so I'll basically have to build a server side web client. I've used HttpClient in Java and something similar in Ruby, but want to make sure it can handle downloads, cookies, and so on.

2- Need to parse and modify Excel (xls and csv) files.

3- Need to take a MS Word file and fill in fields (the gray box type you can insert in Word).

4- Would like to convert Word to PDF.

I would prefer to use Rails but at this moment Grails seems to be the best option because I know HttpClient and Apache's POI and HSSF libraries. Any advice or better options?

+1  A: 

You might want to have a look at Open Office Java Api

In my company we successfully used it for generating documents based on templates filling-in the values of the fields and converting Word documents in PDF format.

Manrico Corazzi