I sharpen three times, then toss. That applies to 1/4" and above , I can not see good enough to sharpen bits smaller. I'm retired, have time and enjoy sitting down and resharpen bits at times.

When I was in business, had a real nice old guy (retired machinest ) come around and sharpen bits very economically.I could not pay someone to sharpen as cheap and good . He came around every month for 15-16 years, then all of a sudden he did not come for 2-3 months, hated to call his wife, and I was right, he passed. His wife proudley told me that at least 25 other shops had called and offered their condolances, and told her what a good job he did..a real craftsman..

Adobe (old as dirt )