Dragons start popping up after you do those quests for Jarl Bagruuf (bring him the Dragonstone, fight the dragon outside Whiterun etc) after which dragons will be randomly encountered. Much like in Oblivion, gates wouldn't start appearing until after finishing Kvatch.
If I buy stuff, Its with metal I've earned in game. I've bought keys on a few occasions, one time I unboxed an Unusual Hat (which was worth 2 buds) and on another I got an Strange Widowmaker (was worth 8 keys at the time). It's safe to say I more than got my monies worth.
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