I've had a couple of different Ink cards and continue to have one open. The annual fees were always charged on the first statement after the annual anniversary of its opening. I find the 5% bonus on cell/phone/Internet charges, not to mention the 2% categories, easily exceed the annual fee.
About transferring your points, what are your interests and needs? I find United points to be the best use of my Ultimate Rewards balance, but some prefer other airlines or even hotels.