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I made my first sales back in 1979, so handwriting was a practical necessity. Back then I was very particular about my pens -- in my case, I wrote almost exclusively with fiber tipped pens -- and wrote in spiral bound notebooks.
These days I write with pen and paper for my first drafts or when I want to capture ideas on the run. It's slower for me than keyboarding, so it's a good match for the "thinking it out while writing" approach I use for first drafts. Transcribing to the computer has never bothered me much, but I never simply transcribe -- for me, this constitutes my first edit.
I should also point out that I write short stories -- I would probably need to be more disciplined If I ever tried a longer work.
As far as buying pens goes, a lot of writers develop superstitions about their writing tools. It's usually pretty harmless. I'm thinking back to my fiber tipped pen days -- these days I've grown out of that phase. They felt comfortable in my hand, I liked the way the ink looked on the paper, I felt more confident knowing I had one or two in my pocket, etc.
If they're inexpensive pens -- live it up! If, on the other hand, you're collecting a drawer full of fine writing instruments, you might need to address your OCD.
I'm not sure I have any tips to impart, but this is how I manage. Good luck with your writing!
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