Thanks pauleckler! Your reply is very helpful. I do have around $30000 in other taxable income. I just thought I might start with RAI as it's my biggest cap-gain stock.

But, I am not the most savvy person when it comes to stocks, funds options etc. Your last paragraph: "And note if you are on Medicare, both capital gains and tax free income count toward the MAGI, which determines if you pay extra high income premiums of up to nearly $3000/yr. You might want to factor this added cost into your calculations too.", Went over my head. I am on medicare, but I don't know what MAGI means. I'm sure I need to know what this is, so please clue me in!

Also, I have never tried "Options". Is this a safe idea for one who only owns stocks?

Thanks,

VJOCO

PS:

I'm from Texas, so no state or local taxes. ;O)