Syncing with iTunes / Are app updates even necessary within the app-aka doesn't work

So whenever I sync / connect my iPhone to iTunes, I notice that a bit part of the lag perhaps is all the apps stored on the desktop. Also, they always 'require' updating for some reason and don't get updated even though I already have an updated copy on my iPhone. Why does iTunes still insist on downloading many apps that need to be updated?? But that's not the real issue here I have.

The real problem is when I click on update all apps on the bottom right of my iTunes window, it always times out downloading or it asks for my iTunes store password every 3 seconds or so or immediately after I enter it and press enter. Can anyone help with the problems I'm having here with the connection? Is this a reason my iTunes is so slow?

I swear it's faster to stream from iCloud with iTunes match than it is to play them directly through iTunes on my desktop.

Frustrated.

Thanks though for all your help if anyone knows what's going on.

 

Is "DO NOT UPDATE APPS AUTOMATICALLY" the actual name of the button? Where is that located in iTunes?

On the iPhone, I don't manually update. I have so many apps that it's a time drain to to sit and evaluate each one every time an update pops up. Usually, when there is something wrong with an app, they get re-updated rather quickly anyway. But that's only on the iPhone side anyway so it has nothing to do at all with the problems in iTunes.

By the way, yes, this has always been the case. Just posted now since today it asked me to enter my iTunes password a million times instead of 10 or so....