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First off, I'd suggest shooting at least one Glock. People seem to love 'em or hate 'em. If you have been shooting something else very much, it may take at least a box of ammo to get acclimated to Glock trigger.

If concealability is a primary concern, yea, the size of the 27 is about as small as they get - but it's still a brick (to me anyway). Lots of folks who get the 27 wind up feeling need for a pinkie extension of some sort - which gets the grip up close to the height of the Model 23.

I had a 23 for around 7 years right after they came out in 1990, but swapped it in on a new Kahr - less capacity, but much flatter.

Biggest question ya might want to ask yourself is " What am I going to be primarily using this for? " Then go see if you can shoot at least one Glock of comparable size and caliber. (The .40 is pretty "snappy" in the 27.)