Unless you are dealing with a very simple web application situation, the actual language you work with isn't very important at all. At least, not the language-as-language. Rather, you should care about the larger environment of your problem.

I would say that the things that you care about more are

• Support from your corporate IT department
• Ability to satisfy customer requirements
• Deadlines, and your familiarity with what you're doing

Support from your corporate IT department

Once you deploy the box with your web solution on it, who will do the backups? Who will manage the its IP configurations? Who will give it a name on the corporate DNS? Who will provide the source data for it, and how will they do it?

Corporate IT.

I've gotten Linux boxes running Apache, MySQL and mod_perl into large corporate environments before, but always in Stealth Mode. Fortunately, the boxes only need servicing about once a year, but if it were any more frequently than that, then very likely we would have played "by their rules." And you can't influence those rules from the outside.

Ability to satisfy customer requirements

In one web project I worked on, I had to generate GIF (later PNG) graphs of business activity on-the-fly to be included in web pages.

Then they told me that they wanted to drag-and-drop those graphs into Excel so that they could manipulate them for other purposes.

Err...

Fortunately, I managed to talk them out of this. The "compromise" was that I showed them how to download the GIFs so that they could include them themselves, and I provided the processed data that I used to make the graphs so that they could generate their own Excel graphs based on that data.

The hell of it is, Microsoft does provide controls that you can plug into IE and IIS and ASP and all that that will let you do exactly what they wanted to do -- honest-to-God drag&drop COM graph objects that they could lift from the web page and put into Excel. If only you go the 100% Microsoft route. The moral of the story: make sure that you know your customer requirements beforehand, so that you can use the technology that will satisfy them.

Deadlines, and your familiarity with what you're doing

If you do have complete control over your project (on a technical front at least), then you have two choices: the "get it done" choice, and the "learning experience" choice. If you want to "get it done", then don't try anything new. Just go with whatever you happen to already know. Otherwise, you have no right to expect that the project will take any less period of time than infinity.

Cheers,
Richard