Depends on the paint job. If going for a pro job, yeah, you may need to pull the race off the fork crown. If it's a home rattle can job, masking it may suffice. If powder coating, it (usually) must be removed.
I purchased an inexpensive puller tool like this $24 one:
crown race tool on amazon
It works best when getting it in place and working the race off by hitting the tool with a rubber mallet.
To reinstall, I use a 9" long section of 1" pvc pipe and the mallet (or floor).