This is just my opinion and experience, but I would not choose to move from Osaka to Kyoto. If you are staying in an Osaka place that you like, do consider just staying there. I feel that by the time I pack, check out of the Osaka hotel, move to the Kyoto hotel, have them hold my luggage because it will be too early to check in, then come back later and check in.....it seems like I've wasted a lot of time that could have been spent doing something interesting in either city.
It really is an easy train ride from Osaka to Kyoto, you can make your daily plans based on weather and what's going on in either city, instead of based on moving to the other city. Thousands of people commute every day between Kyoto and Osaka for work, shopping, and meeting friends. (which does mean you will be on a train with a lot of other people if you travel during rush hours....but that in itself is a cultural experience!!)