I'm assuming your 5.3 machine is your development environment and your 2011 is your production environment and your request to send some delta items to your production environment.  

It is possible to upgrade from 5.3 sp1 straight to 2011, I'd recommend getting your environments at the same version, which will make it possible for you to content port from one 2011 environment to the other.

Perhaps if you put some more information here you might get a better answer from the community.

what is best way to Migrate Content from Tridion 5.3sp1 to 2011sp1
I have an app that doesn't properly stop listening on a port.

How do I force it to stop so I can open the application again/use that port again?
