Pardon me for not being clear. Tried doing a single payment at the end of the year, but NOT having made sufficient estimated payments throughout the year. I'd have to look back to see if those were properly set up as W2 wages from an S-Corp. That's been a couple of years ago and I don't recall the details.
Are you saying that making a single salary payment at the end of the year with appropriate withholdings covering the full amount is acceptable practice? I can see if there was an employment agreement that stated that the salary was yearly, paid on Dec. 31, maybe that works. The only real benefit there is keeping the capital in the business throughout the year, though. Unless I'm actually using it all actively, I'm not sure it's much of a benefit over taking more frequent distributions/salary.
In the case of the gambling business, if I'm keeping that money in use as stake money, then yes waiting has value, but I'm finding it's not likely to be the scenario. I can keep $20-50K in play at any given time, so if money starts growing beyond that substantially, I'd rather move it to long-term investment vehicles.
