hey @jasonshick,
the user needs to get hold of 5$ value of STEEM via an exchange, or an existing Steem user. For example, you can sign up a friend via your referral link, pay for him the STEEM amount and get 5$ cash from him.
Credit card would come down the road.
For the apple watch, yes the plan is to have the integration in the coming 2 months. Right now we are working on Fitbit being available on iOS in the coming week (it already is on Android), Garmin next, and then apple watch.