Interesting re: skipping quarterly taxes and taking the hit on the small penalty. I wonder if it would raise suspicion if you just stop paying estimates and pay up in April.
FWIW, Ally bank has a 3% savings account atm, so you could easily make up that penalty by parking your future tax payments in a high yield savings.
Couple states I've lived in, missed payment penalties are 10% of what was owed. Parking, say, $3k at 3% for a few months to net ... $100 to then pay a $300 fine doesn't seem to make much sense.
I've missed payments, and paid the fines, and typically it's a small % of the total tax burden, so it's not hit me hard, but I wouldn't plan to explicitly withhold payments to try to pick up small % in savings.
FWIW, Ally bank has a 3% savings account atm, so you could easily make up that penalty by parking your future tax payments in a high yield savings.