The answer depends on the overall shape of the cabinets, what you can afford, and what style you are drawn too. Sometimes there is compromise - sometimes the budget and style don't match:)

If you do not like the wood cabinets and can afford new, then get new rather than paint. Painting over previously finished cabinets is a good way to give new life to worn cabinets and get through several more years till new cabinets can be purchased. However, I've seen many cabinet paint jobs that started to need touch ups after 3 years (often sooner), major touchups after 5, and not looking so great at all after 10. A lot of that depends on family life situation - lots of young kids vs. single older person.

To be honest - your kitchen looks very good and I would not "update" because of a vague notion that things out to be updated:) That is marketing 101 - get people to feel their present stuff is not quite the thing so they will go out and buy more stuff. If you really prefer a different style, check your budget and do some research, but don't go all gray and white because of HGTV. The trend will be different in a few more years - already moving away from one trend and new looks become popular. One can't keep up, so it is best to discover your preferred style and stick with it or at least avoid over trendy materials (like weathered gray floors) that are not flexible style wise.

The only thing I would change is the microwave to a vent and that is only because I am short and like good venting when I cook - totally personal reason. I might change the backsplash to a more simple cream subway tile - again only because that is my personal favorite. The stone up the wall for backsplash is probably more upscale then my tile.

As to floor - the style of floor you have is like a traditional hardwood floor. It is a style that has been around over a hundred years so more timeless then trendy. If it is holding up well for you, then leave it till you need new.