I'll answer the question re pocket 9mm...
As a long-time Kahr fan. I have always liked the PM9. They now have a CM9 that is about $100 less, and I wouldn't be afraid to go with that.
Currently, I am relying on a Keltec PF9. It has been 100% reliable so far with several hundred rounds through it - but it isn't built for longevity (per the manufacturer's info). Got a chance to inspect and dry-fire the Ruger LC9, and if I were looking to replace the PF9 right now, that is what I would go with. Sized right, priced competitively, better trigger and sights than the PF9, and Ruger's CS is about as good as Keltec's - and both are a bit better than Kahr's.
Prices for the above range about from $250 to $430.
If you are looking at something a little less compact - or if money is no object, you get a lot more good choices.
