Some thoughts:
If all your music is on your hard drive, and you are working on your laptop while playing music through your USB DAC, I suggest you get the music off of your hard drive and onto an external drive, because your hard disc gets hit a lot as you work on stuff, and this gets in the way of the audio signal.
External drive should use a different bus than your USB DAC, as I posted above.
iTunes does not load music into RAM and playback from RAM, it hits the drive where the music is stored (I think). JRiver has a check-box to playback music from memory, try checking this box to get rid of ticks and pops. Also adjust the buffering from the default 6 seconds to 10 or 20 seconds, if you can stand it. This is all under tools->options->settings.
Hearing a difference between lossless and lossy file formats is highly dependent on the quality of compression, the signal path/settings in the computer, and the quality of the system you are using, there are many, many variables.
I doubt you need special drivers, Windows 7 supports audio output up to 24bits/96kHz. If you get into some 24/192 or 24/384 high res files, from HD Tracks and the like, you might need special drivers, depending upon your DAC.
One more thing, at the risk of angering the budget audio gods, I have found that the USB cable counts. Big time. I have heard a vast difference in sound quality between USB cables in my system, I suggest Pangea PC, they are cheap, $25 for 0.5m at Audio Advisor, silver plated copper cable. You can return it if you don't hear an improvement over stock USB.
Sheesh this post is getting long, sorry about that. JRiver will also auto-detect the bit rate and sampling rate of your music track, and will adjust its output to match. iTunes will not do this. If you are only running 16/44.1 music rips, do not allow Windows to up-sample that output. Let your DAC do it, and set windows to output 16/44.1, if your DAC will take it. You want the computer doing as little as possible to the audio signal, turn off all processing.