Apartment Guru: Make the Apartment Search Less Painful

Dear Apartment Guru,

I have been looking for a new place to live and it has been one ordeal after another. I know apartment hunting is hard, but does it have to be this soul-crushing? I don't have to move but I really want to. Any tips for how to make looking for an apartment less depressing and stressful?

I'd appreciate any insight you have!

--Just Looking for a Place to Lay My Weary Head