I am in the tIRA withdrawal camp. In December, after making our Roth conversion, I withdraw enough to have the federal and state taxes withheld to meet a "safe harbor". Yes, I need to account for this when I make the conversion, leaving enough room in the tax bracket. But, it is simple, requires no quarterly payments, and keeps me "aware" of our tax liability. When we get to the point of taking SS, I will probably have the withholding cover most of the tax.
If I need to pay at tax time, and that is the case this year (for state taxes), I efile, use the ACH method and let the feds/state pull from the account. Yeah, I pay for the state efile, but if $19.99 is going to be a big deal, I am not FI.
Is this safer than sending a check? I don't know, but it is simpler.