Given a web application that would need to run on the customer's servers, and installed by the system administrators on the customer's side, which technology stack would result in an easier deployment with least amount of "server surgery" done by the sysadmins?
Our target platforms are Windows/IIS/SQLServer and Linux/Apache/MySQL, but since the customer's web server host could be anything from a freshly opened Windows box to a fully patched and up-to-date Ubuntu machine, we're trying to find the technology which would result in least amount of work for the system administrators (read, minimize our support requirements).
The typical options are, of course, PHP, Python, ASP.Net (running Mono for the Linux installations), Rails, Java, etc.
Some of the things to consider would be whether an average "out of the box" web server running IIS or Apache would have the required libraries to install the product if it were built using one technology rather than another. For example, a PHP-based solution would probably be easier for the customer to deploy on a Linux machine as opposed to having to install mono and whatever other dependencies would be required to run an ASP.Net solution on a Linux machine as a web app.
Aside from that, there are questions of having the right balance between "out-of-the-box" functionality and "easy-integration", such as: would an included web server be of help? Or does that just make things more confusing when Apache is already running on port 80?
We're working on the assumption that the customer has some access to a system administrator, but perhaps not a full-time/dedicated one -- something like a shared web host account.
Given that, we want the customer to be able to have the least amount of friction in installing the web app on their web server, and we're debating the right technology stack to use for that.