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I'm starting to like it. It is the middle names of my father in-law George Alan and Uncle Mark Allen This is also my brother in-laws first name. Alan Timothy

I find it dated. I think I might prefer the spelling Allen, but I don't really think it's especially cool. Alain is a bit better.

1. Yes
2. I think of dark hair, dark eyes, and handsome (since the name means little rock or handsome)
3. Possible combos for Alan:
Alan James
Alan Robert
Alan Kenneth
Alan Shane
Alan Noah
Alan Thomas
Alan Samuel
Alan Gregory
Alan Derek / Derrick
Alan Nathaniel
Alan Patrick
Alan Luke / Alan Lucas
Alan Matthew
Alan Timothy
Alan Rhys
Alan Bradley
Alan Blake
Alan Gabriel

Alan! A childhood friend and neighbour, I see him so clearly now. so, yes, I like the name, always have.
Sibset?-Alan and David.
Alan, Roderick and Johanna.
Alan, Cassandra and Elizabeth. (always called Beth.)

Alan seems very bland and white-bread to me, also the name of a middle-aged man. It's hard to imagine a little boy with the name.

I like it a lot. I think it works well with classic names or more unique Irish and Scottish names. It seems to have the same flavor as James to me, but it is less popular where I live.

For some reason I classify Alan with Brian, Colin and Denis/Dennis (the A,B,C,D thing is entirely coincidental!). I think of those names as having the same vintage and all remind me of middle-aged men in knitted cardigans. Not sure why. Having said that, Alan and Colin are the two of that quartet that I don't really mind, in contrast to the others.
Alan was brought to England by the Bretons/Normans so it is a well-established historic name. I marginally prefer the Allan spelling that the Scots favour, and I quite like the Welsh Alun.
Allen is nice too, but perhaps too much the surname version and too similar to Ellen.