the only thing a cobalt bit will do for you is, providing you dont break or burn the bit up, it will stay sharp longer than a regular bit. a quality HSS bit is fine for the type of stainless work that is usually required on any boat or boat project...
mills and repetitive hole drilling is different and may require a cobalt bit.
but still, with all that said, a set of cobalt bits are nice....
so even though stainless steel doesnt necessarily need a cobalt bit, a slow drill speed is absolutely mandatory, and a water soluble cutting oil helps keep it cool and lubricates the bit (water soluble because a water based oil/agent will carry heat away faster and better than a petroleum based oil), but even water is better than drilling dry... once you start the hole, dont stop, keep drilling so if there is any heat building up, you may be able to stay ahead of it with the cutting edge of the bit
when stainless steel is acutely heated quickly by a drill turning too fast, or by being worked with a hammer or bent back and forth, it will "work harden" the metal so that nothing will cut into it short of a grinder....
so, in short, if you try to drill too fast and without a cooling agent, the metal can become so hard that before you get all the way thru, your bit will burn and heat the metal so that another try at the hole is futile.
be careful when the bit breaks out the other side of the work that the bit does not actually break... this is the only time to lighten up on the pressure during the drilling process.
after a few messed up holes and quite a few bits, you will be an expert at drilling stainless...
