Well 1.8 came out in November

It's already January and Dragonborn will be coming out soon. So will update 1.9 come out at the same time?
I'm worried my 50+ mods will not work together (and cause ctds) when the update comes

The 1.8 patch was supposed to prepare the game for Dragonborne. However, the EXE files are usually replaced with new DLCs, so it is possible the mods that you are using will have to be addressed.

This is why I don't mod my games until the DLC season is over or almost over.