ROBERT MORTON  I had used version 2 and it worked great when I lost a hard drive. I really didn't use it for regular syncing though. Of course years later I had another need for it. I also had lost my registration number. The developer responded with my registration information in less than 4 hours on a Sunday. That is what I call great support from a product that does its job very well.  
(Version 4.1.4)

TALLAN  People ask why pay so much for this program? Well, it works and has continued to do so for five years. The developer has always gotten back to me within hours, usually within minutes, when I've had an issue; one time he developed a "mini-fix" on the fly for me that allowed me to keep going rather than make me wait for the general release update.

Also the program is under constant development and is continually improved. The speed of file transfers has gotten much much faster in recent months, the interface has been totally redesigned, and when new versions of iTunes or OS X are released that "break" the older version of iPod.iTunes an update is usually available within 48 hours.

I use a $24.95 program on the Windows side to do the same tasks; imagine my dismay after buying the new Nano to find that this (Windows) program knew nothing about duplicates and I had to spend time going through my music library deleting dupes one at a time. That's not a problem with iPod.iTunes which while eliminating duplicates is smart enough to know that a song at 192kbps is NOT the same as the same song at 224kbps, and that you might want both.

I've tried a lot of the cheap and free iPod transfer programs over the years but have found nothing that offers anything close to the power, flexibility, and support of iPod.iTunes - sometimes you really DO get what you pay for.  
(Version 4.1.1)

SILKY SLIM  PodWorks does not handle multiple playlists as of yet, therefore iPod.iTunes is a good solution, and if you can charge X amount of dollars and still get buyers, then great. Safe to say that is what microsoft has done to you Cougar!, When instead of wasting your money on office you could have downloaded for free "open office" or even buy the much cheaper and better "iWork".  
(Version 3.8.1)

COUGARBLUE  Can we get past the seemingly mandatory explanation that the iPod doesn't sync in both directions and thusly we need a helper app? That said, Senuti is free, I had no problems in recovering the 5581 songs lost when my hard drive took a dive using Senuti. Hats off to anyone who cares enough about the community to donate their work.

For more functions, iPodWorks is a great $8 option.

I can't explain the technical aspects of iPod or iTunes song filing functions, but if I can get the job done for either nothing or $8 why the heck would I want to spend $39?

I wish the developer well, however this is too much for a one trick pony, I only spent $129 for my copy of Microsoft Office.

And one more thing, please no more kissy-kissy reviews from developer 'friends", I still won't pay you $39.  
(Version 3.4.4)

TONYBOY  This software looks like EXACTLY what I need to share my music library between my home and my work computer. It would solve a big headache I've had in managing my music library.

But it costs 29€, and there's no way I'm paying that much for something that I might even be able to write myself.

Sorry, but no...  
(Version 3.4.1)

THEMTB  This software seems to have quite a few reviews that sound like they are written by the developer or someone involved in the app.

Macupdate should check it out. Especially Sevren, the guy that knew the developer by name and a few others that only reviewed this and no other program.  
(Version 3.3.7)

THEMTB  $39 is not shareware. That is software that you get a CD, a pretty box and pay retail for. This is a $10 app.

It seemed to work but wouldn't sync a bunch of my songs because it was an unregistered copy.

This app also phones home so make sure you have Little Snitch turned on.  
(Version 3.3.7)

MACCENTRIC  To answer the original question, the iPod can only sync in 1 direction, this let's you sync the ipod back to iTunes.

There are much cheaper alternatives, even free options to do this. $39 is way too much, even half that is pushing it with alternatives such as iPodRip and el iPodo available.  
(Version 3.3.7)

MACINTARD  Just putrid. Will not run at all, just crashes and says variable not defined. Of course, it won't run long enough for me to define any damned thing.  
(Version 3.3.6)

SEVREN  I've been using this useful tool since version 2.7.3 and have been thouroughly impressed. I have a desktop Mac at home, a desktop Mac at work, and an iBook, all of which I use to play songs from iTunes. Using this tool makes it a snap to sync my songs and playlists. Think of it as .Mac for your iTunes music. But at a one-time low price. The Customer Service has been excellent as well. My email was responded to the same day within an hour or two.  
(Version 3.1)