I think people who enjoy dynamic typing have had bad experiences with bad static type systems earlier (C, C++, Java).
Once you use a good static type system (ML, OCaml, Haskell) you see that dynamic typing isn't responsible for the joy, but the ability to express rich ideas without repeating redundant type declarations.
I think when the first dynamic programing language was invented, the loose typing system must be thought as a big advantage.
Type checking is necessary in some cases, but I really enjoy dynamic typing a lot. So I think a bit tradeoff like this is acceptable. After all, we have to tradeoff everywhere when it comes to computer science such as the time-space tradeoff of an algorithm.