I've never had to pay for my own MSDN, IDE or server while I was in the Microsoft development ecosystem. In many cases, my employer would pay for those things, and it was usually generously flexible - i.e. I could build Windows machines and install Office at home off those licenses. The Community edition of Visual Studio has been sufficient for quite some time, though I'm sure there are cases where it is not.

Anyone running a copy of Windows could run a free copy of SQL Server (Express) and SQL Server Studio, IIS Express and the .NET Framework using VS Community to build MVC apps. You would use the Web Platform Installer for just about any of those things.

Between https://dotnet.microsoft.com/apps/aspnet (previously https://asp.net) and https://www.microsoft.com/web/downloads/platform.aspx it's generally very easy to dip your feet in the waters.

(All that being said, I'm now in the NodeJS ecosystem. It's... interesting!)