Arc Web Services is going away and is now becoming ArcGIS online.
This means a whole new updated sdk for developing arc web applications for web sites.
If you need a really advanced routing system developed a company called routesmart makes dll based route solver solutions for client server apps and now web applications using ArcGIS 9.x
All ESRI api's are complex. You have to just start using it and when you gain experience in it you will feel more comfortable.
Since ESRI has somewhat of a shrinking monopoly on certain aspects of GIS capabilities it will be interesting to see what Google and others develop to create some decent competition for the GIS world. Until then all encompassing GIS solutions will not be flexable or easy to work with and expensive.
One major gripe I have with ESRI products is rather ethereal however it seems to be a recurring theme I have experienced in all of their product lines.
You do a code\db\whatever update and test. It doesn't work. You try again without making changes and it still doesn't work, but if you try one more time it suddenly works.
It's like ESRI has coded everything to fail 2 times first before any change to a point release, mxd, sde data, or python code to begin performing as intended. As strange as this may seem if you have ever worked with their products you know this because you have experienced it yourself. This may have to do with my lack of understanding but all my GIS friends tend to agree with me on this point.