Some finance ramblings for Friday afternoon

Ahhh, it's a slow Friday in the city, can't wait to get out of the office, hit the gym (I've lost three pounds in two weeks- yeah!) and then enjoy a lazy Friday night, free of airports and train stations and packing suitcases.

A few things I've been thinking about:

1) Should I invest in a Roth rather than Traditional 401k?
I called my parents yesterday to share with them the good news of my awesome summer bonus and my dad made some joke about finding a way to fool the tax-man... my mom, on another phone in the house, promptly told me not to listen to him, since she doesn't want her only daughter to end up in jail... funny, my parents, these days... But then I asked my dad his opinion on Roth vs. Traditional, and he is of the mindset that taxes are likely to go up, as they've not only been much higher in the past, but the nature of the changing demographic will also likely require taxes to be higher, as well (more elderly people to support, no social security, etc.). I read a timely analysis by Dog Ate my Finances on the cost effectiveness of Roth vs. Traditional if taxes stay the same, and so really the only factor I'm gambling on are that tax rates will go up, which I am willing to bet. (Either that, or I am planning to be in a higher income-tax bracket at the time). I was originally contributing to a pre-tax 401k to minimize the impact to my bottom line, since I needed the extra cash. Now that I've gotten a raise, I think I can afford to deduct a bit more from my paychecks next year. I'll keep you updated, but since I've already maxed out my 401k for the year, it will be next year's business.

2) Why was my cash rebate so low on my Discover Card statement last month?
I never blogged about this mystery, but I found out the answer and will share it with you. My Discover Card statement last month was a hefty $660 or so, but my cash back reward was only $1.41 :(.... Turns out that Discover Card has a pro-rated cashback bonus schedule, as follows:

$0 - $1,500: Earns 0.25%
$1,500.01 - $3,000: Earns 0.5%
$3,000.01 +: Earns 1%

I've definitely spent more than $3,000 on my Discover Card this year with all of my traveling, but it turns out that my "anniversary" with the card is June 25, which is why my July purchases only accrued .25% in cashback awards. Oh well, at least that answer makes sense.

3. How do I actually deduct my losses in the stock market from my taxes?
I have no idea. I know I have to sell my stocks at a loss first, but do I have to sell my winners, too, and write off the difference? I'm confused, but since I've lost a lot of money in the stock market this year (although I'm not exactly sure how much), I might as well take advantage of this tax benefit if I can. But part of me wants to hang onto the losers until they become winners again :)