Which distro and DE? And what kind of customizations?

ubuntu (yeah..  I know) and gnome.

trying to install wms, realized it is too much work. 

installed customs font, GTK theme, icon theme as well. 

I really dig awesome WM but it seems has a pretty deep learning curve. 

maybe one day I will use it and ditch Gnome once and for all. 

I like the simplicity of the tiling window manager. like I can switch between workplaces within a second 

Nothing wrong with Ubuntu at all. 19.10 is the best yet, IMO and I'm confident 20.04 will be a nice improvement from 19.04.

Fonts and themes shouldn't break anything, provided they are officially supported. If not, well, that is a risk of course. Gnome is a bit limited and buggy in that respect, I've found. If you really want to go crazy with DE mods and custom themes, but want to stick with a Ubuntu-based distro, try Kubuntu. It's Ubuntu with KDE instead of Gnome. KDE is one of the most customizable DE's out there and has tons of supported themes for just about every aspect.

Tiling WM's is a whole other thing that's becoming more popular and yeah, they take time to learn. I tried i3 a couple times, but just ended up going back to a more conventional DE. It all depends on what fits your workflow best.

My current customized Manjaro KDE:

holy shit. did you post this on reddit sometime earlier? I saw it on unixporn

Yep, I did.

fuck. actually met someone here whos also on reddit... 

hope yo udont happened  to know my username there. LOL