What Environment Fits Best

I have been a developer for a LONG time. Started back with DBase and FoxPro many years ago, then to PowerBuilder and the past 11 years doing Java. In fact I was an early Java adopter, back in the SWING/awt and servlet days.

I have a product idea in mind, and I am looking for advice on where to go with it. I am looking to do the following automatically:

Login to a website (info stored locally or on my own website)
or possibly create and account on a website.
Pop a dialog to fill out or use Decaptcher when prompted.
Fill in data and save the application.

Assuming you are logged into an account, it will goto a certain link that has a list, select an item on the list, then fill out a form with 3 fields. One field a textfield, one a radio button (always the same option to choose), and fill in a textarea. Each loop through will contain the same date entered in each field.

It will need to iterate through the list N times.

Potentially allow the use of multiple accounts per workstation so would need ability to use proxies to eliminate ip banning.

I want this to be a stand alone and lightweight application that can be easily propagated to numerous users, so want to maximize the number of users available. Java is too high maintenance (versioning...) so would want something that is a quick install and off the user goes.

I have seen Adobe AIR applications and have heard of people using UBot for this type of thing.

Any suggestions? Looking to either pick up the technology myself or sub out to a developer.

This is not a BH request, just trying to automate a task that I currently do manually. If you have used the likes of SEO Link Robot, similar to the Social Bookmarking piece but for a single specific website for social propagation of info.

Thanks!