Not intending to sound pompous about it, but I think after you've grown enough plants, you do get the "feel" for how much water a certain size plant in a certain size container might need after so many days under specific wetaher and growth conditions. THEN, chances of success with containers withOUT drainage holes would be better.
A container with drainage hole(s) sitting (raised) in an appropriately sized drip tray is MUCH MUCH easier to maintain, with better margin for -- and recourse -- in case of an error. That's not just MHO -- "It's a FACT." (try that in Marisa Tomei voice from My Cousin Vinnie