how easy/hard is it to get from beginning to end? Trying to figure out the best place to dump a car before soloing so that i can get back to it?

we put one car at the start, and one at the end, then drove between one way and rode the other. Dumping in eastbourne is easy, but you probably don't want to have to have any hassle after a long day in teh saddle

You can get a train back to Winchester from Eastbourne. You have to change 3 (I think) times, and it takes ages but it gets there eventually.

You have to change trains twice, once at Brighton, and once either at Southampton, or between Havant and Southampton to get onto the S'ton-London line to Winchester. It takes "a while" check your train times as you don't want to get stranded!