Originally Posted by card1953
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3. Does it make sense to buy 10k points for $100, or should I perhaps get a HHonors Amex? Or is there a way to use coupon connection, or perhaps transfer points from AA (I think the exchange rate isn't too favorable)?
Coupon Connection is an option. There are multiple people out there with trades for eRewards which can be exchanged for up to 3000 HH points. A couple of small trades would erase your deficit.