And I'm sure your early inclinations were then confirmed when they released 2.0 and their superb implementation of generics :)
I had been a longtime Perl hacker (it was a thing back then) and was still cutting my teeth on the cost/benefit tradeoffs of strongly-typed languages. I remember being quite frustrated in 1.x while attempting to write a data-access layer and having to use lots of casts to write reusable code.
It definitely took me longer than I'd like to admit to wrap my head around the usefulness of generics, but I certainly remember the "aha" moment I had when I realized how much cleaner they'd make my codebase.
In fact, I ended up completely dropping the code-generation tool I had written -- in Perl, of course :) -- to create the base classes which could work directly with our strongly-typed models.
> ASP.Net Webforms with AJAX being a particularly frustrating story
Very much agreed; I avoided using .NET for anything in any way web related until MVC came out. Working with those Microsoft black box server controls was just too much.
> like the .NET Core launch and migration-strategy not being all that convincing
I can forgive that, since it looks like their migration strategy with the upcoming .NET Standard 2.0 will be much more solid.