Don't worry, I'm a Glock and HK guy too so your not going to hear any needless anti-Glock comments coming from me. I also am not going to berrate your choice of caliber. However I am going to give you an honest assement of both pistols in comparison to one another.
The major difference in the Glock and the HK is the grip. The P2000 in particular has a great grip but it may take you a while to get used to the angle. As far as field stripping, it's virtually the same on both pistols. Take out the slide lock on an HK and the slide comes off, disassembly is identical to the Glock from that point on. In my eyes its easier to go from Glock to HK then it is to go vice versa. I think thats why so many die-hard HKers dislike the feel of the Glock.
If you decide to go Glock again, get the G23. I own both a G19 and a G26 and if I had to pick one it would be the G19. The G19 is not much larger than the G26 and as hard as I try I cannot justify sacrificing 5 rounds of ammo for the small reduction in size/weight that the G26 offers. The G23 is a compact like the G19 and is easy to conceal.
The P2000 is a great handgun (I've never fired an SK). It is also light and easy to conceal and the option of having the LEM trigger is a big plus if you like DAO. If you favor the .40 then the full size P2000 would probably manage the muzzle flip better than the SK.
I use Speer Gold Dot as my carry ammo. Out of the Subcompact (G27 or P2000sk) I prefer the "short barrel" stuff because it performs a little better. For carry ammo always go with a hollow pointed round, preferbly jacketed which is a must for the Glocks.