Edit: I was really referring to language families, so including things like OCaml, Modula, etc.
The frontend is usually the hard part IMO. In WebKit, we have 100,000 lines of code for our "frontend" (i.e. the DFG compiler) and 50,000 lines of code for our "backend" (i.e. B3). That split is really interesting.
Far as Ada, I figured it would be difficult due to the large number of language features and complexities of analyzing a program for safety w/ all its rules. And any interactions that might emerge in that between features and rules. Could be easier than I think but my default belief is that it's not easy.
Frontend was awful and I never finished it, but the LLVM-style backend wad very easy to build.
Is that really the case? It seems to me that a Prolog-like resolution system, coupled with a constraint solver, would get most of the job done with little effort.
There are certainly many rules to keep track of, but in some cases the newer rules are strict generalisations of the older rules. For example, Haskell's original type classes are just a special-case of modern multi-parameter, flexible instances/contexts, etc. type classes. Likewise, we can implement constraint kinds, type class instance resolution and type equalities using one constraint solver.
My usual approach to implementing a type system is to derive a flat list of Prolog equations out of the AST and leave it to Prolog for solving. If you ask what to do with error messages, I've got a comprehensive answer, but it is not for a mobile phone typing.
My approach to the typing error reporting is quite compatible with the Prolog codegen. What I do: for each AST node which produce one or more type equations I record the location data (cache it and give it an index), and then issue a Prolog term like this: with_location(Id, Term), for each of the terms generated by this location.
with_location semantics is simple, but may depend on the presence of a backtracking. If it's a plain Hindley-Milner, there is no backtracking, and it simply do call/1(Term), continue if true, store Id and the failed term with all the current bindings and fail/0() if false.
If there is a backtracking, I store a stack of location ids and failure reasons instead, but this required patching the Prolog execution engine a little bit (luckily, I'm using my own Prolog for this).
Now, the next step is to decipher the failed term. Most of the equations are in a trivial form: equals(A, B), so I simply report that prolog_to_type(A) failed to unify with prolog_to_type(B). For the other (rare) kinds of equations I define custom pretty-printing rules.
To me this is the difference between knowing that your program will probably work after it compiles, vs not knowing until after its deployed.
What I think people really enjoy in dynamic languages like JavaScript is the instant feedback, just reloading the browser. This can be accomplished with decent IDEs for most statically typed languages.
Which ones are these? All of the statically-typed and well-designed languages I can think of are, at the least, hard to compile well, if not hard to compile in the first place. (Haskell and Rust both come to mind; there are few Haskell compilers other than GHC, and no Rust compilers other than rustc.) The languages that are easier to compile are either not statically-typed in a useful way, or not well-designed, or both.