If I had a time machine, I'd probably go to 2000 first. It'd be more to check the machine was working and to gather data related to the next jump. The next jump however would be dependent on the data gathered from the first jump. Yes, it would be to achieve a better timeline, as this one is likely to head towards a dystopia. The actual aim of the first few jumps would be to give myself more time before the dystopia and to gather more information and improve the time travel technology that I would be using, ie be able to jump further, and faster. I imagine that several divergence points would have to be altered, and I'd probably have to alter several percent of history or something. It's possible even that I may never personally reach the goal but another me does, that said, leaving information for the other me's would probably make it more likely that I reach it and so do they, but the question remains would my other selves do that as well or prevent me's from reaching it?
So based on current knowledge JUMP_YEAR - 2000 - ~1950 - JUMP_YEAR - Unknown
In other words, I would have to continuously have to jump back and forwards to get to 0% divergence from the central worldline. (My guess is that we are at ~5% currently)
Perhaps, it just depends.