It definitely depends on the stage you're at in your life.
I have had my dream scope since 1997 now. I spent about $12K on a Tak FS128 and a heap of astrophotography gear. But back then I had no wife, no kids and a very understanding bank manager
.
I don't think I need a different OTA but would like to upgrade the mount to something way better one day. But now I have wife and two kids in high school so all purchases are on hold for years to come. Earning way more money, sure, but also have much bigger financial commitments.
If money was not an issue I don't know what I'd do. Probably call Claude and see if he can order me one of those 300mm Tak refractors that you sometimes see pictures of. Nah, I'll get two of 'em and get Kunama to make it into a bino-scope for me