I work on 1099 of which I hate, but I have a good paying job for now while always looking for that perm spot again like I had pre 9/11.  In any case I will owe the IRS loads of money in April and I will have some but will certainly owe 10's of thousands of dollars and won't have the full amount by 4/15.  I had actually planned to pay off the CC's and just worry about making the payment arrangements with the IRS (as I did in 2007) on the balance I will owe and thus be behind once again as I was last year and not paying quarterly.  I know I will have penalties but I was told it would be easier to work with the IRS to pay them and thus it would be my only debt.  I own nothing and just rent an apartment in NYC.  I do get some write-offs but very little to make a huge dent in the actual taxes due on around a 150K.  I also take care of a parent and two older sick siblings but that is again out of pocket since I have no medical insurance and I am not the home owner or power of attorney over my family but I am the only one who can help financially thus it is a huge draw on my income verses being able to set aside quarterly taxes.  I use to do my own taxes but this is too difficult now and easier to go to H&R or some accountant.  Thanks for any advice or opinion.