Taking up the guitar later in life.

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After 5 days my fingers are killing me, but I'm enjoying it.

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Keep at it. You need to build callouses. Not only do they stop that pain, but they make it easier to play (nobody uses a soft slide...).

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Is there a moment when things start to click?

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Really, the biggest aha moments come with learning different scales and keys. As far as technique goes, it's all about practice. It builds strength and muscle memory. It's a slow, gradual process. Being a drummer in the past, you should at least have decent wrist control for strumming and picking.

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Can I be a decent player before I'm 50?

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Yes. Will you? That's up to you. Practice practice practice.

I'm 60, I picked up my first guitar at age 53. I'm self-taught and after 7 years, I'm an ordinary strummer. Despite my limitations I enjoy playing—that's the important thing—and I play every day. I also like writing my own songs, so that's an extra incentive.

I'm not especially musically inclined, so I figure if a shlub like me can play, just about anyone can. If you pick up the instrument as late as I did, you probably won't be the next Jimmy Page or Eric Clapton. But if you enjoy playing, that's all that matters.

Don't worry about the sore fingers, etc. Keep playing and that'll go away.

An instructor at a course I went to opened up the morning with a beautiful classical guitar piece. He then told us he 53 y/o, and at age 47 decided to learn the guitar. He took lessons for 5 years before playing that piece for us, but yes, it can be done.