You seem to have been in the field of Oracle for a long time. Though a lot of debate is already there on the Internet on comparisons of Oracle and other databases, I still want to know where you put Oracle depending upon your experience.
Before the release of SQL Developer/JDeveloper, etc., Oracle tools were the least user-friendly and had cryptic usage, whereas Microsoft products have been user-friendly, and in the world of IDEs, they simply know the nerves of the programmers.
Today also, you see powerful, intuitive front-ends like VB.NET and compare with Java counterparts. Java is not meant to be a language for desktop IDEs. It is very slow as compared to VB.NET.
Similarly, working with SQL Server is simple. Oracle is an enterprise database and powerful but why has it never been user-friendly?
I'm not sure exactly what your question is, but I can expand some on what you have said.
One of Microsoft's biggest strengths has been its ability to connect all of their product lines. This means that you can call OS libraries and SQL Server libraries all from the same VB application. SQL Server works well on Windows and VB works well with all of the above. Microsoft enjoys this interoperability and takes advantage of it (yet some would say that this interoperability leads to many security holes). And being Microsoft products, the tools are GUI-based. Oracle, on the other hand, has traditionally been command-line-based. I administer both SQL Server and Oracle, and at times, I like the GUI tools at my disposal, and at other times, I like the command-line tools that I use. Each has its strengths and its weaknesses. For instance, in SQL Server, I use Enterprise Manager because I can easily point and click my way to some specific admin task without having to look in the documentation for the way to perform that task. But in Oracle, I favor SQL*Plus because I find the command-line interface to be faster to use. If you know your SQL statements well, SQL*Plus is much faster for the Oracle DBA. I guess it all depends on your point of view. I don't think there is a right or wrong here.