Part of why I've always liked the Microsoft stack is that historically they've always had excellent documentation. (I taught myself C++ with the VS 6 documentat

Part of why I've always liked the Microsoft stack is that historically they've always had excellent documentation. (I taught myself C++ with the VS 6 documentation) While not up to their old standard, their current documentation is still many times better than many open source and new/trendy technologies. I know you requested non-obvious recommendations, but the fastest way to get up to speed is literally to read the docs. I'd avoid .NET Core for now and let things settle first. So http://www.asp.net/aspnet http://www.asp.net/aspnet C# is close enough to Java that just pretending it is Java will get you 90% of the way, and reading the ASP.NET docs (in C#) will expose you to enough that you shouldn't need to study it specifically.