I am currently going through the same issue! I have an in-grown related cyst that has been consistently swelling and draining for the past 2 years! After a recent visit to the gyno, where she told me there is not much I can do, she suggested visiting the dermatologist mainly because she was worried the ingrown could get infected and cause a bigger issue.
I visited the dermatologist last week and they did a preliminary check-in on the issue. I’m currently taking an antibiotic to help the swelling go down (it has subsided quite drastically), but I have my follow up tomorrow! I’ll follow up with any new info they may give me tomorrow, but I would say it’s worth a visit to the dermatologist if they are getting too painful or are reappearing constantly.