We use console applications also. If you use logging tools like Log4net you can properly monitor their execution. Also, I'm not sure how they are more difficult to maintain than a web page, given you may be sharing some of the same code libraries between the two if it is designed properly.
If you are against having those tasks run on a timed basis, you could have a web page in your administrative section of your website that acts as a queue. User puts in a request to run the task, it in turn inserts a blank datestamp record on MyProcessQueue table and your scheduled task is checking every X minutes for a new record in MyProcessQueue. That way, it only runs when the customer wants it to run.
Hope those suggestions help.