Taxes 2 Questions

CFD244 said
It's a good idea to owe them as much as you can at the end of the year. A big refund just means an interest free loan to the Government. Just make sure that you are diligent enough to have the dough on hand when the bill comes in.:)

Not exactly the same, but I have been in "1099" territory a few times
Independent contractor type deal

I'd make sure that for each paycheck that came in from that job 25% got put in a dedicated account right off the bat

Then when taxes came due, I'd have pretty close to that exact amount sitting in that account