It's not like Sun took a gun to everyone's head and said "use Java, damn it". I mean, Microsoft might try that :-), but Java succeeded almost despite Sun (e.g. on its own merits as a language), instead of because of them.
And really it was Sun's bungling of the language evolution that led to Java's lack luster reputation today. In constract, Microsoft did a very admirable job with evolving C# to keep up with more modern syntax/semantic expectations.
I suggest that Java mostly caught on for two reasons (from a purely technical perspective):
1. It had automatic garbage collection.
2. It had a batteries-included approach to its standard library.
In practice, both of these had caused much pain for C and C++ programmers for a long time, and a platform where things Just Worked was very appealing for a lot of those programmers. That in turn led to non-technical advantages that drove the widespread adoption of Java for server-side/enterprise programming.
I don’t see that either of those technical advantages has much to do with the type system, though. In fact, of all the programming languages and type systems I’ve used, Java’s is probably still the worst by almost any interesting measure.
I don’t really accept the original premise that static typing is making a comeback; it never went anywhere. However, if it’s gaining renewed interest in certain parts of the industry, I suspect that has more to do with increasing experience of where dynamic typing can have disadvantages as more projects using it grow larger and are maintained for longer, and perhaps to some extent with aspirational statically typed languages like Haskell showing that some of the perceived disadvantages of static type systems are not inherent problems.
It is better these days, but even today Java programs tend to have more distribution issues than other languages.
In the olden days, besides the awful Swing GUI that made it immediately recognizable, gray squares and/or stack dumps when trying to execute Java applications or applets were common.
I would love to have a mainstream development stack with the kind of programming tools and expressive power that plenty of modern languages and libraries now offer, but which ultimately produced compiled and statically linked executables the old-fashioned way at least by default, without necessarily relying on package managers or heavyweight virtual machines or run-time linking or writing code just to describe how to install my code. Unfortunately, I doubt that such a language/tool chain exists today, though I’m optimistic that sooner or later someone’s promising niche language will break through.