As for Ise, we had a similar itinerary as yours. After a full day of sightseeing in Kyoto we went to Ise in the evening. We stayed at Hoshidekan which I would recommend if you are looking for a budget ryokan option.
Next day we saw Kawasaki in the morning (ca. 9am to 10am), late breakfast, then the two Ise Shrines (ca. 11am to 1pm), Oharaimachi (ca. 1:30 to 2pm), Mikimoto Pearl Island (ca. 2:30 to 4pm; which I would not recommend); late lunch and Meoto Iwa (around sunset, i.e. 6pm) before taking one of the last train connections home to near Tokyo (later options would have existed if we were to go to central Tokyo).
Generally a very enjoyable day, and we even happened to see the then to-be prime minister Yukio Hatoyama at the Ise Shrines!
If you can leave Osaka in the evening before, a similar itinerary should be certainly possible. Even if you can leave only on the same day, the main parts should be possible if you start early. As you can see from above timings we did not get up extremely early on that day.