I second a good 22 to start, such as the Ruger. I went with a used Mark II in SS for mine. Pros and cons to the various Mk versions (I, II, III and IV); do your research and decide which is most important to you.
As for the second pistol, it is hard to beat the the recommendation of the CZ75 or 85 (difference being ambidextrous safety for lefties on the 85). Used ones can be found in your budget range. The nicest thing about the CZ's is the grips fit almost every hand size equally well. They are also very reliable. Some of the main reasons why it is used by more police and military forces around the world.
If you can, try both the 9mm and the 40 before making your buying decision. Buy a couple of boxes of each in different bullet weights so you can feel the difference between them for yourself.
Myself, I pefer the 40 S&W over the 9mm, but that is just me. Mine is the SP-01 Tactical. I started with a 75 in 9mm, and then had a 85 in 40 after that. Never should have sold the 85, as it was a dual tone. Am happy with the SP-01, and will not part with this one. I like the extra weight of the all steel pistol and the extra weight of this one with the rail.
Revolvers are also good. I like the Ruger Blackhawks, and now have 2 in the 41 Rem Mag. But if you are looking for a dual action, the GP100's are great revolvers and you can shoot the 38 Spcl in the 357 Mag. Used revolvers can also be found for reasonable prices in either model.