question about use of multiple libraries

I'm planning putting two copies of music on my computer, one in a lossless format and another in a lossy format for my ipod. However, I dislike having two copies of every song present in my library since it makes things look more cluttered. I've experimented with creating another library in itunes and putting my lossless files in this, converting to lossy, and moving the lossy files to my other itunes library. This is kind of a pain though. I know lots of people here have two copies of their music, lossless and lossy, so I'm curious to see how you do it and rather you use multiple libraries or have everything in one.

 

I've heard about these things you can use that transcode your music before it goes on your ipod. Since I have a PC what you use obviously wouldn't work for me. However, I've heard of other programs such as anapod explorer that can do this. I don't really care to use one of these programs though. For one thing I don't want to pay for it. I also like having all of my music in one place and not using more than one program to play it, transfer it, etc. It's just too bad itunes won't give you the option of doing this. I suppose I could always just put all my lossless music in my main library, convert to lossy format, put these tracks on my ipod, and then delete the lossy music from the computer....... Would that work or would it cause problems when I connected my ipod again.