splitting resort stays/late arrivals

[time4Mickey]

We had thought about splitting our stay between 2 resorts which we have never done before. I am now thinking we may fly so we arrive in the evening and thought maybe we could stay at a value resort the first night then switch. This could mean 3 different resorts in 7 nights. Has anyone done that? Plus how late does the magical express run? Is there any added problems with arriving late in the evening. We have never done this before.
We would either stay at a hotel close to the airport or at Disney so thought this would be better.

Thanks.