So I've gotten to testing Codeweavers 19 and Catalina today. It works great to run DDO in Catalina. In fact, it runs far better than the official Mac DDO client does in HS for me.

Now the downside. I did some reading up, it looks like crossover's method to get wine running in Catalina was pretty hacky requiring a special compiler to be made for creating some libraries, and unfortunately is not going to even make it into development wine for a good long time.

I can't recommend enough using Codeweavers now for Catalina users.

https://www.codeweavers.com