If the ways aren’t already too dry, then the color of the previous oiling will tell you when it needs more. Very dark or black oil on the sliding surfaces or feed screws are a sure sign the machine isn’t being oiled well enough. Oil performs two basic functions, the lubrication of course, and excess oil helps flush out the machines own wear particles and any contamination from swarf. So over oiling a bit while seemingly wasteful is still a good habit. If the fresh oil isn’t remaining clean after a short period of use, then it’s overdue for a partial disassembly and a thorough and detailed cleaning.
Even G. Thomas mentions doing so for his Super 7 after turning cast iron. For manual machine tools, I think the manufacturer’s do a rather poor job of even mentioning that machine tool slides, feed screws and nuts do require a partial disassembly and manual cleaning in solvent every so often. And the same for a lathes tail stock quill, feed screw and nut. Reading the Connely book Machine Tool Reconditioning was more than enough to completely change my previous habits about slide cleanliness and lubrication.