Originally Posted by xooz

To be helpful, it would be good to know:
- The approximate total spend you expect to make on the card(s)
- Whether you have any other source of points/miles, such as you already travel for business and would accrue xx,xxx miles or points
- Type of personal travel you would intend to take (intl vs domestic, general locations of interest, etc)

In general, if you are looking to get points to assist in both air and hotel travel, it seems the Starwood Amex card might be a better, single card as it can be used for air travel, while HH points cannot. This is not what I do, but I only want to maximize hotel stay opportunities, so what you really want to do with the points will make a difference in what would be the best approach.

There are some fantastic threads you can find via the search function that discuss card based point accrual. Recommend you search those out and read through them as background.