Expertise and speciality

To answer number 1: the difference between "expertise" and "specialty" is that you can have expertise in many areas. Your specialty is your primary area of focus.

Regarding number 2: I'd recommend "expertise" as it allows you to enumerate the various areas in which you have skill. In fact, I'm not sure I've ever seen "specialty" used in a CV. It's certainly uncommon. But "expertise" is quite usual.

Expertise with MS Word, Photoshop, and similar software.

Also, the term "speciality" is preferred UK usage, whereas US standard is "specialty."

"Specialty" is a special subject of study, line of work, area of interest, or the like i.e. His specialty is art criticism.
However, this doesn't mean that someone's specialty is their expertise, or in other words, just because someone is interested in a particular subject or area doesn't mean they are experts on that area. i.e. Jame's specialty is making terrible milkshakes. His expertise is research on nanotechnology.

In resumes, "experience, or skills and experience" is generally used for people who are students, graduates, or new workers, where as "expertise" is used only when the person is on a senior or professional level.