First time posting, about the last time I try to fix iTunes before I give up

Question

I'm probably not going to make friends amongst the Apple-o-philes. PC user. deal with it; iPhones were sold to us as platform independent; iTunes is offered as a product that works with Windows. OK. I bought into it; my third iPhone, got one for my girlfriend, got 4,000 songs in iTunes. And I find rather than my Apple product making my life better, faster, quicker, stronger, more efficient, I'm spending hours every month doing things I've done or had to do now a dozen times. Every time there is an update, now I have three computers to update and it totally scrambles my music library with now four copies of every file.
Eventhe Apple boards I see online say "Oh, it will take you a few hours, but it's worth it"
That's not the point - why is it neccessary? Arent computers the kind of thing you'd use to sort through a list of 10,000 anythings and let the processor find the 2,500 you want so a human doesn't have to waste "a few hours"????
That there is now an aftermarket program offered for sale at $20 or more to fix the problems with iTunes libraries should embarass someone imprtant at Apple. It surely makes a good argument why we don't see the "I'm a Mac"/"I'm a PC" ads, because my Mac products (iPhones/iTunes) have cost me a lot of money, and taken a lot of my time.' at this point as much if not more than my 3 PC's. My frustration has brought me to tears, and unfortunately in the wake of the death of Steve Jobs, I'm going to say something that may sound "too soon" or at least sacreligious:
If I have "Manage music manually" checked, why can't I just click-and-drag a song straight from Windows into iTunes.? Onto my iPhone? 
I mean it was Macintosh that brought the world the computer mouse, at least how most of us learned to use one is because Mac had it first. Click and drag is something that came first to Mac OS, second to Windows.
Why can I not drag a song, a podcast, a movie, from it's Windows location to iTunes, drop it on my iPhone and find it on the phone? Why do I have to go through this "sync" madness to risk wiping my phone clean in the process (as it did once already)? Why does "manually manage music" do no good, because if I drag a song anywhere onto the iTunes window, i Can't drop it anywhere.
I magange to get a Bachelor's degree from a Big Ten university, in of all things Computer Graphics Design. My experience with iTunes and my iPhone at times make me feel like someone must have dressed me in the morning and fed me liquid food through a straw because surely someone this hapless is too hopeless to chew and swallow on his own.
Next, Apple wants me to pay for the cloud, pay for support by the call, pay $40 for a new cord every time the dog chews one or when it comes apart on it's own (which any cable that costs $40 ought not to do under normal use) -
I feel used by Apple. I used to love my original iPod, right now I feel like a stooge and I'm having confidence issues about life in general because iTunes has broken my spirit, and the money-sink reality of this thing is making me glad the cassette deck in my car still works and my mix tapes just don't disappear like my playlists.
Should I just kill myself? This is almost a serious question - because I go up an ddown these forums and I see hundreds, thousands of questions - spent two hours looking for an answer before I posted this one - I can't find an answer. 

Answer 1

I'm probably not going to make friends amongst the Apple-o-philes. PC user. deal with it; iPhones were sold to us as platform independent; iTunes is offered as a product that works with Windows. OK. I bought into it; my third iPhone, got one for my girlfriend, got 4,000 songs in iTunes. And I find rather than my Apple product making my life better, faster, quicker, stronger, more efficient, I'm spending hours every month doing things I've done or had to do now a dozen times. Every time there is an update, now I have three computers to update and it totally scrambles my music library with now four copies of every file.
Eventhe Apple boards I see online say "Oh, it will take you a few hours, but it's worth it"
That's not the point - why is it neccessary? Arent computers the kind of thing you'd use to sort through a list of 10,000 anythings and let the processor find the 2,500 you want so a human doesn't have to waste "a few hours"????
That there is now an aftermarket program offered for sale at $20 or more to fix the problems with iTunes libraries should embarass someone imprtant at Apple. It surely makes a good argument why we don't see the "I'm a Mac"/"I'm a PC" ads, because my Mac products (iPhones/iTunes) have cost me a lot of money, and taken a lot of my time.' at this point as much if not more than my 3 PC's. My frustration has brought me to tears, and unfortunately in the wake of the death of Steve Jobs, I'm going to say something that may sound "too soon" or at least sacreligious:
If I have "Manage music manually" checked, why can't I just click-and-drag a song straight from Windows into iTunes.? Onto my iPhone? 
I mean it was Macintosh that brought the world the computer mouse, at least how most of us learned to use one is because Mac had it first. Click and drag is something that came first to Mac OS, second to Windows.
Why can I not drag a song, a podcast, a movie, from it's Windows location to iTunes, drop it on my iPhone and find it on the phone? Why do I have to go through this "sync" madness to risk wiping my phone clean in the process (as it did once already)? Why does "manually manage music" do no good, because if I drag a song anywhere onto the iTunes window, i Can't drop it anywhere.
I magange to get a Bachelor's degree from a Big Ten university, in of all things Computer Graphics Design. My experience with iTunes and my iPhone at times make me feel like someone must have dressed me in the morning and fed me liquid food through a straw because surely someone this hapless is too hopeless to chew and swallow on his own.
Next, Apple wants me to pay for the cloud, pay for support by the call, pay $40 for a new cord every time the dog chews one or when it comes apart on it's own (which any cable that costs $40 ought not to do under normal use) -
I feel used by Apple. I used to love my original iPod, right now I feel like a stooge and I'm having confidence issues about life in general because iTunes has broken my spirit, and the money-sink reality of this thing is making me glad the cassette deck in my car still works and my mix tapes just don't disappear like my playlists.
Should I just kill myself? This is almost a serious question - because I go up an ddown these forums and I see hundreds, thousands of questions - spent two hours looking for an answer before I posted this one - I can't find an answer.