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I like the idea of anther pmd, but the second was so amazing that it doesn't seem like it could actually be topped. I would hate for one to come out and be a big disappointment.
Definitely, generation 3 and 4 both have three new games and two remakes, Maybe it will be the same for the 5th generation. Especially with the absence of a GBA slot on the DSi now the third gen games can't be played on newer systems. So I would expect to see them sometime after...
I think it is personal preference. Sure, Yellow is one of the more popular 1st and 2nd gen games, but many people just enjoy the older games more and that is why they play them. Although I must say, Yellow, being so different from Red and Blue, never really got a remake as Firered and Leafgreen...