Any type of game can be done in RM, they may just need a lot of work with scripts.
Dating sim should be relatively easy as that requires just a lot of text and show choices - you could do that without scripts.
As for program suggestions - it depends on your skill as an artist. If you're comfortable with those programs, a lot of people use either GIMP (free) or Photoshop. If you need a character generator because your artistic skills are not up to creating new sprites, then there are several on the internet, the build-in generator from Ace or the GCH on the store.