Three Questions!

I'm new to making servers and not a super expert with computers or wiz or whatever, but anyways I want to know three three things. I have a bunch of plugins and don't want to update them manually every time either Minecraft or the Bukkit builds so can if I just delete the current Build and replace it and run the server will it crash due to outdated plugins?
Second, I have hamachi and it's causing a whole lot of lag and like 10 second intervals to what people see other people doing so I want to know if port forwarding is my only option.
Last, i would love to know if there is something that can automatically update plugins FOR me. Thanks Guys!

 

No u need to download the latest version of the plugin, manually

 

But you can however just update the bukkit builds. Usually 95% of them doesn't break. And if a plugin doesn't work you can always still update it.

 

CraftBukkitUpToDate.

 

If I run my server with a plugin that breaks because it is out of date will my server crash or just run without the plugin?

 

It can't really break.. nah.

 

Run without it. Worst case scenario it'll spam your console with errors. But it'll run.

Just start it up and if no plugins are disabled during start up or give errors then you're good to go.