I am asked, when the customer wants to drill their own holes, and have been asked many times; "Do I need a special drill bit to drill stainless steel?" I just tell them you need a good quality drill bit and lubricant. The reason they ask is their experience(s) based on lack of experience are many dull, low quality drill bits. Quality HSS steel cutters have parameters that fit a wide range where speed and feed make the difference, along with lubricant making the difference in how long they last, how many holes, etc. We have many discussions on the use of carbide cutters and the supporting arguments come across as someone making excuses for a prodigal child. Buying anything used leaves one guessing, especially in regards to how it was used, is it dull and so on, but if the deal is good, go for it. There's no experience gained in using a dull cutter with no knowledge in what or how it happened to be dulled. If I start with new I learn; **Don't do that again** if I dull it, or buy this again if I'm still making holes after 100+. Buying new on the other hand should be done to fit the job you have, not the job(s) you may have.
With the full understanding this is a hobby, there's too many charts available showing materials and cutting tools to use for there to be any second guessing. A known quality tool is hard to beat. Coatings on cutting tools (my experience) may improve the cut or assist with chip control, but if there is significant cost involved I'll pass. My experience to date puts coatings in general, into a sales feature category. I prefer to spend on a lubricant suited for the material.