Is your first mileage earning card an Amex, Diners, or MC/Visa?

If you already hold one MC/Visa, the Starwood Amex might be a good one for you to have. Lots of flexibility: you can go with hotel stays if you need them, or go to AA with your 20k-25k conversions if you are closing in on 1MM AA Lifetime.

I held the DL Amex card for one year and earned some huge bonuses. It was worth the $85 one time, but would not have been worth it ongoing. Starwood Amex is easier to swallow: first year free, then $30/year (unless they've changed that).

I currently hold the AA Mastercard. I find it to be worth the $50/year because it's the only MC I've held in the past five years that has pretty good customer service. There are occasionally discounted-mileage awards for cardmembers, but I've never been able to take advantage of them. I will cross 1MM on AA within a year, and I may reevaluate whether I need the card after that.